Network Working Group                                 J. Klensin, Editor
Request for Comments: 2821                             AT&T Laboratories
Obsoletes: 821, 974, 1869                                     April 2001
Updates: 1123
Category: Standards Track


                    Simple Mail Transfer Protocol

Status of this Memo

  This document specifies an Internet standards track protocol for the
  Internet community, and requests discussion and suggestions for
  improvements.  Please refer to the current edition of the "Internet
  Official Protocol Standards" (STD 1) for the standardization state
  and status of this protocol.  Distribution of this memo is unlimited.

Copyright Notice

  Copyright (C) The Internet Society (2001).  All Rights Reserved.

Abstract

  This document is a self-contained specification of the basic protocol
  for the Internet electronic mail transport.  It consolidates, updates
  and clarifies, but doesn't add new or change existing functionality
  of the following:

  -  the original SMTP (Simple Mail Transfer Protocol) specification of
     RFC 821 [30],

  -  domain name system requirements and implications for mail
     transport from RFC 1035 [22] and RFC 974 [27],

  -  the clarifications and applicability statements in RFC 1123 [2],
     and

  -  material drawn from the SMTP Extension mechanisms [19].

  It obsoletes RFC 821, RFC 974, and updates RFC 1123 (replaces the
  mail transport materials of RFC 1123).  However, RFC 821 specifies
  some features that were not in significant use in the Internet by the
  mid-1990s and (in appendices) some additional transport models.
  Those sections are omitted here in the interest of clarity and
  brevity; readers needing them should refer to RFC 821.






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  It also includes some additional material from RFC 1123 that required
  amplification.  This material has been identified in multiple ways,
  mostly by tracking flaming on various lists and newsgroups and
  problems of unusual readings or interpretations that have appeared as
  the SMTP extensions have been deployed.  Where this specification
  moves beyond consolidation and actually differs from earlier
  documents, it supersedes them technically as well as textually.

  Although SMTP was designed as a mail transport and delivery protocol,
  this specification also contains information that is important to its
  use as a 'mail submission' protocol, as recommended for POP [3, 26]
  and IMAP [6].  Additional submission issues are discussed in RFC 2476
  [15].

  Section 2.3 provides definitions of terms specific to this document.
  Except when the historical terminology is necessary for clarity, this
  document uses the current 'client' and 'server' terminology to
  identify the sending and receiving SMTP processes, respectively.

  A companion document [32] discusses message headers, message bodies
  and formats and structures for them, and their relationship.

Table of Contents

  1. Introduction ..................................................  4
  2. The SMTP Model ................................................  5
  2.1 Basic Structure ..............................................  5
  2.2 The Extension Model ..........................................  7
  2.2.1 Background .................................................  7
  2.2.2 Definition and Registration of Extensions ..................  8
  2.3 Terminology ..................................................  9
  2.3.1 Mail Objects ............................................... 10
  2.3.2 Senders and Receivers ...................................... 10
  2.3.3 Mail Agents and Message Stores ............................. 10
  2.3.4 Host ....................................................... 11
  2.3.5 Domain ..................................................... 11
  2.3.6 Buffer and State Table ..................................... 11
  2.3.7 Lines ...................................................... 12
  2.3.8 Originator, Delivery, Relay, and Gateway Systems ........... 12
  2.3.9 Message Content and Mail Data .............................. 13
  2.3.10 Mailbox and Address ....................................... 13
  2.3.11 Reply ..................................................... 13
  2.4 General Syntax Principles and Transaction Model .............. 13
  3. The SMTP Procedures: An Overview .............................. 15
  3.1 Session Initiation ........................................... 15
  3.2 Client Initiation ............................................ 16
  3.3 Mail Transactions ............................................ 16
  3.4 Forwarding for Address Correction or Updating ................ 19



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  3.5 Commands for Debugging Addresses ............................. 20
  3.5.1 Overview ................................................... 20
  3.5.2 VRFY Normal Response ....................................... 22
  3.5.3 Meaning of VRFY or EXPN Success Response ................... 22
  3.5.4 Semantics and Applications of EXPN ......................... 23
  3.6 Domains ...................................................... 23
  3.7 Relaying ..................................................... 24
  3.8 Mail Gatewaying .............................................. 25
  3.8.1 Header Fields in Gatewaying ................................ 26
  3.8.2 Received Lines in Gatewaying ............................... 26
  3.8.3 Addresses in Gatewaying .................................... 26
  3.8.4 Other Header Fields in Gatewaying .......................... 27
  3.8.5 Envelopes in Gatewaying .................................... 27
  3.9 Terminating Sessions and Connections ......................... 27
  3.10 Mailing Lists and Aliases ................................... 28
  3.10.1 Alias ..................................................... 28
  3.10.2 List ...................................................... 28
  4. The SMTP Specifications ....................................... 29
  4.1 SMTP Commands ................................................ 29
  4.1.1 Command Semantics and Syntax ............................... 29
  4.1.1.1  Extended HELLO (EHLO) or HELLO (HELO) ................... 29
  4.1.1.2 MAIL (MAIL) .............................................. 31
  4.1.1.3 RECIPIENT (RCPT) ......................................... 31
  4.1.1.4 DATA (DATA) .............................................. 33
  4.1.1.5 RESET (RSET) ............................................. 34
  4.1.1.6 VERIFY (VRFY) ............................................ 35
  4.1.1.7 EXPAND (EXPN) ............................................ 35
  4.1.1.8 HELP (HELP) .............................................. 35
  4.1.1.9 NOOP (NOOP) .............................................. 35
  4.1.1.10 QUIT (QUIT) ............................................. 36
  4.1.2 Command Argument Syntax .................................... 36
  4.1.3 Address Literals ........................................... 38
  4.1.4 Order of Commands .......................................... 39
  4.1.5 Private-use Commands ....................................... 40
  4.2  SMTP Replies ................................................ 40
  4.2.1 Reply Code Severities and Theory ........................... 42
  4.2.2 Reply Codes by Function Groups ............................. 44
  4.2.3  Reply Codes in Numeric Order .............................. 45
  4.2.4 Reply Code 502 ............................................. 46
  4.2.5 Reply Codes After DATA and the Subsequent <CRLF>.<CRLF> .... 46
  4.3 Sequencing of Commands and Replies ........................... 47
  4.3.1 Sequencing Overview ........................................ 47
  4.3.2 Command-Reply Sequences .................................... 48
  4.4 Trace Information ............................................ 49
  4.5 Additional Implementation Issues ............................. 53
  4.5.1 Minimum Implementation ..................................... 53
  4.5.2 Transparency ............................................... 53
  4.5.3 Sizes and Timeouts ......................................... 54



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  4.5.3.1 Size limits and minimums ................................. 54
  4.5.3.2 Timeouts ................................................. 56
  4.5.4 Retry Strategies ........................................... 57
  4.5.4.1 Sending Strategy ......................................... 58
  4.5.4.2 Receiving Strategy ....................................... 59
  4.5.5 Messages with a null reverse-path .......................... 59
  5. Address Resolution and Mail Handling .......................... 60
  6. Problem Detection and Handling ................................ 62
  6.1 Reliable Delivery and Replies by Email ....................... 62
  6.2 Loop Detection ............................................... 63
  6.3 Compensating for Irregularities .............................. 63
  7. Security Considerations ....................................... 64
  7.1 Mail Security and Spoofing ................................... 64
  7.2 "Blind" Copies ............................................... 65
  7.3 VRFY, EXPN, and Security ..................................... 65
  7.4 Information Disclosure in Announcements ...................... 66
  7.5 Information Disclosure in Trace Fields ....................... 66
  7.6 Information Disclosure in Message Forwarding ................. 67
  7.7 Scope of Operation of SMTP Servers ........................... 67
  8. IANA Considerations ........................................... 67
  9. References .................................................... 68
  10. Editor's Address ............................................. 70
  11. Acknowledgments .............................................. 70
  Appendices ....................................................... 71
  A. TCP Transport Service ......................................... 71
  B. Generating SMTP Commands from RFC 822 Headers ................. 71
  C. Source Routes ................................................. 72
  D. Scenarios ..................................................... 73
  E. Other Gateway Issues .......................................... 76
  F. Deprecated Features of RFC 821 ................................ 76
  Full Copyright Statement ......................................... 79

1. Introduction

  The objective of the Simple Mail Transfer Protocol (SMTP) is to
  transfer mail reliably and efficiently.

  SMTP is independent of the particular transmission subsystem and
  requires only a reliable ordered data stream channel.  While this
  document specifically discusses transport over TCP, other transports
  are possible.  Appendices to RFC 821 describe some of them.

  An important feature of SMTP is its capability to transport mail
  across networks, usually referred to as "SMTP mail relaying" (see
  section 3.8).  A network consists of the mutually-TCP-accessible
  hosts on the public Internet, the mutually-TCP-accessible hosts on a
  firewall-isolated TCP/IP Intranet, or hosts in some other LAN or WAN
  environment utilizing a non-TCP transport-level protocol.  Using



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  SMTP, a process can transfer mail to another process on the same
  network or to some other network via a relay or gateway process
  accessible to both networks.

  In this way, a mail message may pass through a number of intermediate
  relay or gateway hosts on its path from sender to ultimate recipient.
  The Mail eXchanger mechanisms of the domain name system [22, 27] (and
  section 5 of this document) are used to identify the appropriate
  next-hop destination for a message being transported.

2. The SMTP Model

2.1 Basic Structure

  The SMTP design can be pictured as:

              +----------+                +----------+
  +------+    |          |                |          |
  | User |<-->|          |      SMTP      |          |
  +------+    |  Client- |Commands/Replies| Server-  |
  +------+    |   SMTP   |<-------------->|    SMTP  |    +------+
  | File |<-->|          |    and Mail    |          |<-->| File |
  |System|    |          |                |          |    |System|
  +------+    +----------+                +----------+    +------+
               SMTP client                SMTP server

  When an SMTP client has a message to transmit, it establishes a two-
  way transmission channel to an SMTP server.  The responsibility of an
  SMTP client is to transfer mail messages to one or more SMTP servers,
  or report its failure to do so.

  The means by which a mail message is presented to an SMTP client, and
  how that client determines the domain name(s) to which mail messages
  are to be transferred is a local matter, and is not addressed by this
  document.  In some cases, the domain name(s) transferred to, or
  determined by, an SMTP client will identify the final destination(s)
  of the mail message.  In other cases, common with SMTP clients
  associated with implementations of the POP [3, 26] or IMAP [6]
  protocols, or when the SMTP client is inside an isolated transport
  service environment, the domain name determined will identify an
  intermediate destination through which all mail messages are to be
  relayed.  SMTP clients that transfer all traffic, regardless of the
  target domain names associated with the individual messages, or that
  do not maintain queues for retrying message transmissions that
  initially cannot be completed, may otherwise conform to this
  specification but are not considered fully-capable.  Fully-capable
  SMTP implementations, including the relays used by these less capable




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  ones, and their destinations, are expected to support all of the
  queuing, retrying, and alternate address functions discussed in this
  specification.

  The means by which an SMTP client, once it has determined a target
  domain name, determines the identity of an SMTP server to which a
  copy of a message is to be transferred, and then performs that
  transfer, is covered by this document.  To effect a mail transfer to
  an SMTP server, an SMTP client establishes a two-way transmission
  channel to that SMTP server.  An SMTP client determines the address
  of an appropriate host running an SMTP server by resolving a
  destination domain name to either an intermediate Mail eXchanger host
  or a final target host.

  An SMTP server may be either the ultimate destination or an
  intermediate "relay" (that is, it may assume the role of an SMTP
  client after receiving the message) or "gateway" (that is, it may
  transport the message further using some protocol other than SMTP).
  SMTP commands are generated by the SMTP client and sent to the SMTP
  server.  SMTP replies are sent from the SMTP server to the SMTP
  client in response to the commands.

  In other words, message transfer can occur in a single connection
  between the original SMTP-sender and the final SMTP-recipient, or can
  occur in a series of hops through intermediary systems.  In either
  case, a formal handoff of responsibility for the message occurs: the
  protocol requires that a server accept responsibility for either
  delivering a message or properly reporting the failure to do so.

  Once the transmission channel is established and initial handshaking
  completed, the SMTP client normally initiates a mail transaction.
  Such a transaction consists of a series of commands to specify the
  originator and destination of the mail and transmission of the
  message content (including any headers or other structure) itself.
  When the same message is sent to multiple recipients, this protocol
  encourages the transmission of only one copy of the data for all
  recipients at the same destination (or intermediate relay) host.

  The server responds to each command with a reply; replies may
  indicate that the command was accepted, that additional commands are
  expected, or that a temporary or permanent error condition exists.
  Commands specifying the sender or recipients may include server-
  permitted SMTP service extension requests as discussed in section
  2.2.  The dialog is purposely lock-step, one-at-a-time, although this
  can be modified by mutually-agreed extension requests such as command
  pipelining [13].





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  Once a given mail message has been transmitted, the client may either
  request that the connection be shut down or may initiate other mail
  transactions.  In addition, an SMTP client may use a connection to an
  SMTP server for ancillary services such as verification of email
  addresses or retrieval of mailing list subscriber addresses.

  As suggested above, this protocol provides mechanisms for the
  transmission of mail.  This transmission normally occurs directly
  from the sending user's host to the receiving user's host when the
  two hosts are connected to the same transport service.  When they are
  not connected to the same transport service, transmission occurs via
  one or more relay SMTP servers.  An intermediate host that acts as
  either an SMTP relay or as a gateway into some other transmission
  environment is usually selected through the use of the domain name
  service (DNS) Mail eXchanger mechanism.

  Usually, intermediate hosts are determined via the DNS MX record, not
  by explicit "source" routing (see section 5 and appendices C and
  F.2).

2.2 The Extension Model

2.2.1 Background

  In an effort that started in 1990, approximately a decade after RFC
  821 was completed, the protocol was modified with a "service
  extensions" model that permits the client and server to agree to
  utilize shared functionality beyond the original SMTP requirements.
  The SMTP extension mechanism defines a means whereby an extended SMTP
  client and server may recognize each other, and the server can inform
  the client as to the service extensions that it supports.

  Contemporary SMTP implementations MUST support the basic extension
  mechanisms.  For instance, servers MUST support the EHLO command even
  if they do not implement any specific extensions and clients SHOULD
  preferentially utilize EHLO rather than HELO.  (However, for
  compatibility with older conforming implementations, SMTP clients and
  servers MUST support the original HELO mechanisms as a fallback.)
  Unless the different characteristics of HELO must be identified for
  interoperability purposes, this document discusses only EHLO.

  SMTP is widely deployed and high-quality implementations have proven
  to be very robust.  However, the Internet community now considers
  some services to be important that were not anticipated when the
  protocol was first designed.  If support for those services is to be
  added, it must be done in a way that permits older implementations to
  continue working acceptably.  The extension framework consists of:




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  -  The SMTP command EHLO, superseding the earlier HELO,

  -  a registry of SMTP service extensions,

  -  additional parameters to the SMTP MAIL and RCPT commands, and

  -  optional replacements for commands defined in this protocol, such
     as for DATA in non-ASCII transmissions [33].

  SMTP's strength comes primarily from its simplicity.  Experience with
  many protocols has shown that protocols with few options tend towards
  ubiquity, whereas protocols with many options tend towards obscurity.

  Each and every extension, regardless of its benefits, must be
  carefully scrutinized with respect to its implementation, deployment,
  and interoperability costs.  In many cases, the cost of extending the
  SMTP service will likely outweigh the benefit.

2.2.2 Definition and Registration of Extensions

  The IANA maintains a registry of SMTP service extensions.  A
  corresponding EHLO keyword value is associated with each extension.
  Each service extension registered with the IANA must be defined in a
  formal standards-track or IESG-approved experimental protocol
  document.  The definition must include:

  -  the textual name of the SMTP service extension;

  -  the EHLO keyword value associated with the extension;

  -  the syntax and possible values of parameters associated with the
     EHLO keyword value;

  -  any additional SMTP verbs associated with the extension
     (additional verbs will usually be, but are not required to be, the
     same as the EHLO keyword value);

  -  any new parameters the extension associates with the MAIL or RCPT
     verbs;

  -  a description of how support for the extension affects the
     behavior of a server and client SMTP; and,

  -  the increment by which the extension is increasing the maximum
     length of the commands MAIL and/or RCPT, over that specified in
     this standard.





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  In addition, any EHLO keyword value starting with an upper or lower
  case "X" refers to a local SMTP service extension used exclusively
  through bilateral agreement.  Keywords beginning with "X" MUST NOT be
  used in a registered service extension.  Conversely, keyword values
  presented in the EHLO response that do not begin with "X" MUST
  correspond to a standard, standards-track, or IESG-approved
  experimental SMTP service extension registered with IANA.  A
  conforming server MUST NOT offer non-"X"-prefixed keyword values that
  are not described in a registered extension.

  Additional verbs and parameter names are bound by the same rules as
  EHLO keywords; specifically, verbs beginning with "X" are local
  extensions that may not be registered or standardized.  Conversely,
  verbs not beginning with "X" must always be registered.

2.3 Terminology

  The key words "MUST", "MUST NOT", "REQUIRED", "SHALL", "SHALL NOT",
  "SHOULD", "SHOULD NOT", "RECOMMENDED", "MAY", and "OPTIONAL" in this
  document are to be interpreted as described below.

  1. MUST   This word, or the terms "REQUIRED" or "SHALL", mean that
     the definition is an absolute requirement of the specification.

  2. MUST NOT   This phrase, or the phrase "SHALL NOT", mean that the
     definition is an absolute prohibition of the specification.

  3. SHOULD   This word, or the adjective "RECOMMENDED", mean that
     there may exist valid reasons in particular circumstances to
     ignore a particular item, but the full implications must be
     understood and carefully weighed before choosing a different
     course.

  4. SHOULD NOT   This phrase, or the phrase "NOT RECOMMENDED" mean
     that there may exist valid reasons in particular circumstances
     when the particular behavior is acceptable or even useful, but the
     full implications should be understood and the case carefully
     weighed before implementing any behavior described with this
     label.

  5. MAY   This word, or the adjective "OPTIONAL", mean that an item is
     truly optional.  One vendor may choose to include the item because
     a particular marketplace requires it or because the vendor feels
     that it enhances the product while another vendor may omit the
     same item.  An implementation which does not include a particular
     option MUST be prepared to interoperate with another
     implementation which does include the option, though perhaps with
     reduced functionality.  In the same vein an implementation which



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     does include a particular option MUST be prepared to interoperate
     with another implementation which does not include the option
     (except, of course, for the feature the option provides.)

2.3.1 Mail Objects

  SMTP transports a mail object.  A mail object contains an envelope
  and content.

  The SMTP envelope is sent as a series of SMTP protocol units
  (described in section 3).  It consists of an originator address (to
  which error reports should be directed); one or more recipient
  addresses; and optional protocol extension material.  Historically,
  variations on the recipient address specification command (RCPT TO)
  could be used to specify alternate delivery modes, such as immediate
  display; those variations have now been deprecated (see appendix F,
  section F.6).

  The SMTP content is sent in the SMTP DATA protocol unit and has two
  parts:  the headers and the body.  If the content conforms to other
  contemporary standards, the headers form a collection of field/value
  pairs structured as in the message format specification [32]; the
  body, if structured, is defined according to MIME [12].  The content
  is textual in nature, expressed using the US-ASCII repertoire [1].
  Although SMTP extensions (such as "8BITMIME" [20]) may relax this
  restriction for the content body, the content headers are always
  encoded using the US-ASCII repertoire.  A MIME extension [23] defines
  an algorithm for representing header values outside the US-ASCII
  repertoire, while still encoding them using the US-ASCII repertoire.

2.3.2 Senders and Receivers

  In RFC 821, the two hosts participating in an SMTP transaction were
  described as the "SMTP-sender" and "SMTP-receiver".  This document
  has been changed to reflect current industry terminology and hence
  refers to them as the "SMTP client" (or sometimes just "the client")
  and "SMTP server" (or just "the server"), respectively.  Since a
  given host may act both as server and client in a relay situation,
  "receiver" and "sender" terminology is still used where needed for
  clarity.

2.3.3 Mail Agents and Message Stores

  Additional mail system terminology became common after RFC 821 was
  published and, where convenient, is used in this specification.  In
  particular, SMTP servers and clients provide a mail transport service
  and therefore act as "Mail Transfer Agents" (MTAs).  "Mail User
  Agents" (MUAs or UAs) are normally thought of as the sources and



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  targets of mail.  At the source, an MUA might collect mail to be
  transmitted from a user and hand it off to an MTA; the final
  ("delivery") MTA would be thought of as handing the mail off to an
  MUA (or at least transferring responsibility to it, e.g., by
  depositing the message in a "message store").  However, while these
  terms are used with at least the appearance of great precision in
  other environments, the implied boundaries between MUAs and MTAs
  often do not accurately match common, and conforming, practices with
  Internet mail.  Hence, the reader should be cautious about inferring
  the strong relationships and responsibilities that might be implied
  if these terms were used elsewhere.

2.3.4 Host

  For the purposes of this specification, a host is a computer system
  attached to the Internet (or, in some cases, to a private TCP/IP
  network) and supporting the SMTP protocol.  Hosts are known by names
  (see "domain"); identifying them by numerical address is discouraged.

2.3.5 Domain

  A domain (or domain name) consists of one or more dot-separated
  components.  These components ("labels" in DNS terminology [22]) are
  restricted for SMTP purposes to consist of a sequence of letters,
  digits, and hyphens drawn from the ASCII character set [1].  Domain
  names are used as names of hosts and of other entities in the domain
  name hierarchy.  For example, a domain may refer to an alias (label
  of a CNAME RR) or the label of Mail eXchanger records to be used to
  deliver mail instead of representing a host name.  See [22] and
  section 5 of this specification.

  The domain name, as described in this document and in [22], is the
  entire, fully-qualified name (often referred to as an "FQDN").  A
  domain name that is not in FQDN form is no more than a local alias.
  Local aliases MUST NOT appear in any SMTP transaction.

2.3.6 Buffer and State Table

  SMTP sessions are stateful, with both parties carefully maintaining a
  common view of the current state.  In this document we model this
  state by a virtual "buffer" and a "state table" on the server which
  may be used by the client to, for example, "clear the buffer" or
  "reset the state table," causing the information in the buffer to be
  discarded and the state to be returned to some previous state.







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2.3.7 Lines

  SMTP commands and, unless altered by a service extension, message
  data, are transmitted in "lines".  Lines consist of zero or more data
  characters terminated by the sequence ASCII character "CR" (hex value
  0D) followed immediately by ASCII character "LF" (hex value 0A).
  This termination sequence is denoted as <CRLF> in this document.
  Conforming implementations MUST NOT recognize or generate any other
  character or character sequence as a line terminator.  Limits MAY be
  imposed on line lengths by servers (see section 4.5.3).

  In addition, the appearance of "bare" "CR" or "LF" characters in text
  (i.e., either without the other) has a long history of causing
  problems in mail implementations and applications that use the mail
  system as a tool.  SMTP client implementations MUST NOT transmit
  these characters except when they are intended as line terminators
  and then MUST, as indicated above, transmit them only as a <CRLF>
  sequence.

2.3.8 Originator, Delivery, Relay, and Gateway Systems

  This specification makes a distinction among four types of SMTP
  systems, based on the role those systems play in transmitting
  electronic mail.  An "originating" system (sometimes called an SMTP
  originator) introduces mail into the Internet or, more generally,
  into a transport service environment.  A "delivery" SMTP system is
  one that receives mail from a transport service environment and
  passes it to a mail user agent or deposits it in a message store
  which a mail user agent is expected to subsequently access.  A
  "relay" SMTP system (usually referred to just as a "relay") receives
  mail from an SMTP client and transmits it, without modification to
  the message data other than adding trace information, to another SMTP
  server for further relaying or for delivery.

  A "gateway" SMTP system (usually referred to just as a "gateway")
  receives mail from a client system in one transport environment and
  transmits it to a server system in another transport environment.
  Differences in protocols or message semantics between the transport
  environments on either side of a gateway may require that the gateway
  system perform transformations to the message that are not permitted
  to SMTP relay systems.  For the purposes of this specification,
  firewalls that rewrite addresses should be considered as gateways,
  even if SMTP is used on both sides of them (see [11]).








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2.3.9 Message Content and Mail Data

  The terms "message content" and "mail data" are used interchangeably
  in this document to describe the material transmitted after the DATA
  command is accepted and before the end of data indication is
  transmitted.  Message content includes message headers and the
  possibly-structured message body.  The MIME specification [12]
  provides the standard mechanisms for structured message bodies.

2.3.10 Mailbox and Address

  As used in this specification, an "address" is a character string
  that identifies a user to whom mail will be sent or a location into
  which mail will be deposited.  The term "mailbox" refers to that
  depository.  The two terms are typically used interchangeably unless
  the distinction between the location in which mail is placed (the
  mailbox) and a reference to it (the address) is important.  An
  address normally consists of user and domain specifications.  The
  standard mailbox naming convention is defined to be "local-
  part@domain": contemporary usage permits a much broader set of
  applications than simple "user names".  Consequently, and due to a
  long history of problems when intermediate hosts have attempted to
  optimize transport by modifying them, the local-part MUST be
  interpreted and assigned semantics only by the host specified in the
  domain part of the address.

2.3.11 Reply

  An SMTP reply is an acknowledgment (positive or negative) sent from
  receiver to sender via the transmission channel in response to a
  command.  The general form of a reply is a numeric completion code
  (indicating failure or success) usually followed by a text string.
  The codes are for use by programs and the text is usually intended
  for human users.  Recent work [34] has specified further structuring
  of the reply strings, including the use of supplemental and more
  specific completion codes.

2.4 General Syntax Principles and Transaction Model

  SMTP commands and replies have a rigid syntax.  All commands begin
  with a command verb.  All Replies begin with a three digit numeric
  code.  In some commands and replies, arguments MUST follow the verb
  or reply code.  Some commands do not accept arguments (after the
  verb), and some reply codes are followed, sometimes optionally, by
  free form text.  In both cases, where text appears, it is separated
  from the verb or reply code by a space character.  Complete
  definitions of commands and replies appear in section 4.




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  Verbs and argument values (e.g., "TO:" or "to:" in the RCPT command
  and extension name keywords) are not case sensitive, with the sole
  exception in this specification of a mailbox local-part (SMTP
  Extensions may explicitly specify case-sensitive elements).  That is,
  a command verb, an argument value other than a mailbox local-part,
  and free form text MAY be encoded in upper case, lower case, or any
  mixture of upper and lower case with no impact on its meaning.  This
  is NOT true of a mailbox local-part.  The local-part of a mailbox
  MUST BE treated as case sensitive.  Therefore, SMTP implementations
  MUST take care to preserve the case of mailbox local-parts.  Mailbox
  domains are not case sensitive.  In particular, for some hosts the
  user "smith" is different from the user "Smith".  However, exploiting
  the case sensitivity of mailbox local-parts impedes interoperability
  and is discouraged.

  A few SMTP servers, in violation of this specification (and RFC 821)
  require that command verbs be encoded by clients in upper case.
  Implementations MAY wish to employ this encoding to accommodate those
  servers.

  The argument field consists of a variable length character string
  ending with the end of the line, i.e., with the character sequence
  <CRLF>.  The receiver will take no action until this sequence is
  received.

  The syntax for each command is shown with the discussion of that
  command.  Common elements and parameters are shown in section 4.1.2.

  Commands and replies are composed of characters from the ASCII
  character set [1].  When the transport service provides an 8-bit byte
  (octet) transmission channel, each 7-bit character is transmitted
  right justified in an octet with the high order bit cleared to zero.
  More specifically, the unextended SMTP service provides seven bit
  transport only.  An originating SMTP client which has not
  successfully negotiated an appropriate extension with a particular
  server MUST NOT transmit messages with information in the high-order
  bit of octets.  If such messages are transmitted in violation of this
  rule, receiving SMTP servers MAY clear the high-order bit or reject
  the message as invalid.  In general, a relay SMTP SHOULD assume that
  the message content it has received is valid and, assuming that the
  envelope permits doing so, relay it without inspecting that content.
  Of course, if the content is mislabeled and the data path cannot
  accept the actual content, this may result in ultimate delivery of a
  severely garbled message to the recipient.  Delivery SMTP systems MAY
  reject ("bounce") such messages rather than deliver them.  No sending
  SMTP system is permitted to send envelope commands in any character





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  set other than US-ASCII; receiving systems SHOULD reject such
  commands, normally using "500 syntax error - invalid character"
  replies.

  Eight-bit message content transmission MAY be requested of the server
  by a client using extended SMTP facilities, notably the "8BITMIME"
  extension [20].  8BITMIME SHOULD be supported by SMTP servers.
  However, it MUST not be construed as authorization to transmit
  unrestricted eight bit material.  8BITMIME MUST NOT be requested by
  senders for material with the high bit on that is not in MIME format
  with an appropriate content-transfer encoding; servers MAY reject
  such messages.

  The metalinguistic notation used in this document corresponds to the
  "Augmented BNF" used in other Internet mail system documents.  The
  reader who is not familiar with that syntax should consult the ABNF
  specification [8].  Metalanguage terms used in running text are
  surrounded by pointed brackets (e.g., <CRLF>) for clarity.

3. The SMTP Procedures: An Overview

  This section contains descriptions of the procedures used in SMTP:
  session initiation, the mail transaction, forwarding mail, verifying
  mailbox names and expanding mailing lists, and the opening and
  closing exchanges.  Comments on relaying, a note on mail domains, and
  a discussion of changing roles are included at the end of this
  section.  Several complete scenarios are presented in appendix D.

3.1 Session Initiation

  An SMTP session is initiated when a client opens a connection to a
  server and the server responds with an opening message.

  SMTP server implementations MAY include identification of their
  software and version information in the connection greeting reply
  after the 220 code, a practice that permits more efficient isolation
  and repair of any problems.  Implementations MAY make provision for
  SMTP servers to disable the software and version announcement where
  it causes security concerns.  While some systems also identify their
  contact point for mail problems, this is not a substitute for
  maintaining the required "postmaster" address (see section 4.5.1).

  The SMTP protocol allows a server to formally reject a transaction
  while still allowing the initial connection as follows: a 554
  response MAY be given in the initial connection opening message
  instead of the 220.  A server taking this approach MUST still wait
  for the client to send a QUIT (see section 4.1.1.10) before closing
  the connection and SHOULD respond to any intervening commands with



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  "503 bad sequence of commands".  Since an attempt to make an SMTP
  connection to such a system is probably in error, a server returning
  a 554 response on connection opening SHOULD provide enough
  information in the reply text to facilitate debugging of the sending
  system.

3.2 Client Initiation

  Once the server has sent the welcoming message and the client has
  received it, the client normally sends the EHLO command to the
  server, indicating the client's identity.  In addition to opening the
  session, use of EHLO indicates that the client is able to process
  service extensions and requests that the server provide a list of the
  extensions it supports.  Older SMTP systems which are unable to
  support service extensions and contemporary clients which do not
  require service extensions in the mail session being initiated, MAY
  use HELO instead of EHLO.  Servers MUST NOT return the extended
  EHLO-style response to a HELO command.  For a particular connection
  attempt, if the server returns a "command not recognized" response to
  EHLO, the client SHOULD be able to fall back and send HELO.

  In the EHLO command the host sending the command identifies itself;
  the command may be interpreted as saying "Hello, I am <domain>" (and,
  in the case of EHLO, "and I support service extension requests").

3.3 Mail Transactions

  There are three steps to SMTP mail transactions.  The transaction
  starts with a MAIL command which gives the sender identification.
  (In general, the MAIL command may be sent only when no mail
  transaction is in progress; see section 4.1.4.)  A series of one or
  more RCPT commands follows giving the receiver information.  Then a
  DATA command initiates transfer of the mail data and is terminated by
  the "end of mail" data indicator, which also confirms the
  transaction.

  The first step in the procedure is the MAIL command.

     MAIL FROM:<reverse-path> [SP <mail-parameters> ] <CRLF>

  This command tells the SMTP-receiver that a new mail transaction is
  starting and to reset all its state tables and buffers, including any
  recipients or mail data.  The <reverse-path> portion of the first or
  only argument contains the source mailbox (between "<" and ">"
  brackets), which can be used to report errors (see section 4.2 for a
  discussion of error reporting).  If accepted, the SMTP server returns
  a 250 OK reply.  If the mailbox specification is not acceptable for
  some reason, the server MUST return a reply indicating whether the



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  failure is permanent (i.e., will occur again if the client tries to
  send the same address again) or temporary (i.e., the address might be
  accepted if the client tries again later).  Despite the apparent
  scope of this requirement, there are circumstances in which the
  acceptability of the reverse-path may not be determined until one or
  more forward-paths (in RCPT commands) can be examined.  In those
  cases, the server MAY reasonably accept the reverse-path (with a 250
  reply) and then report problems after the forward-paths are received
  and examined.  Normally, failures produce 550 or 553 replies.

  Historically, the <reverse-path> can contain more than just a
  mailbox, however, contemporary systems SHOULD NOT use source routing
  (see appendix C).

  The optional <mail-parameters> are associated with negotiated SMTP
  service extensions (see section 2.2).

  The second step in the procedure is the RCPT command.

     RCPT TO:<forward-path> [ SP <rcpt-parameters> ] <CRLF>

  The first or only argument to this command includes a forward-path
  (normally a mailbox and domain, always surrounded by "<" and ">"
  brackets) identifying one recipient.  If accepted, the SMTP server
  returns a 250 OK reply and stores the forward-path.  If the recipient
  is known not to be a deliverable address, the SMTP server returns a
  550 reply, typically with a string such as "no such user - " and the
  mailbox name (other circumstances and reply codes are possible).
  This step of the procedure can be repeated any number of times.

  The <forward-path> can contain more than just a mailbox.
  Historically, the <forward-path> can be a source routing list of
  hosts and the destination mailbox, however, contemporary SMTP clients
  SHOULD NOT utilize source routes (see appendix C).  Servers MUST be
  prepared to encounter a list of source routes in the forward path,
  but SHOULD ignore the routes or MAY decline to support the relaying
  they imply.  Similarly, servers MAY decline to accept mail that is
  destined for other hosts or systems.  These restrictions make a
  server useless as a relay for clients that do not support full SMTP
  functionality.  Consequently, restricted-capability clients MUST NOT
  assume that any SMTP server on the Internet can be used as their mail
  processing (relaying) site.  If a RCPT command appears without a
  previous MAIL command, the server MUST return a 503 "Bad sequence of
  commands" response.  The optional <rcpt-parameters> are associated
  with negotiated SMTP service extensions (see section 2.2).

  The third step in the procedure is the DATA command (or some
  alternative specified in a service extension).



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     DATA <CRLF>

  If accepted, the SMTP server returns a 354 Intermediate reply and
  considers all succeeding lines up to but not including the end of
  mail data indicator to be the message text.  When the end of text is
  successfully received and stored the SMTP-receiver sends a 250 OK
  reply.

  Since the mail data is sent on the transmission channel, the end of
  mail data must be indicated so that the command and reply dialog can
  be resumed.  SMTP indicates the end of the mail data by sending a
  line containing only a "." (period or full stop).  A transparency
  procedure is used to prevent this from interfering with the user's
  text (see section 4.5.2).

  The end of mail data indicator also confirms the mail transaction and
  tells the SMTP server to now process the stored recipients and mail
  data.  If accepted, the SMTP server returns a 250 OK reply.  The DATA
  command can fail at only two points in the protocol exchange:

  -  If there was no MAIL, or no RCPT, command, or all such commands
     were rejected, the server MAY return a "command out of sequence"
     (503) or "no valid recipients" (554) reply in response to the DATA
     command.  If one of those replies (or any other 5yz reply) is
     received, the client MUST NOT send the message data; more
     generally, message data MUST NOT be sent unless a 354 reply is
     received.

  -  If the verb is initially accepted and the 354 reply issued, the
     DATA command should fail only if the mail transaction was
     incomplete (for example, no recipients), or if resources were
     unavailable (including, of course, the server unexpectedly
     becoming unavailable), or if the server determines that the
     message should be rejected for policy or other reasons.

  However, in practice, some servers do not perform recipient
  verification until after the message text is received.  These servers
  SHOULD treat a failure for one or more recipients as a "subsequent
  failure" and return a mail message as discussed in section 6.  Using
  a "550 mailbox not found" (or equivalent) reply code after the data
  are accepted makes it difficult or impossible for the client to
  determine which recipients failed.

  When RFC 822 format [7, 32] is being used, the mail data include the
  memo header items such as Date, Subject, To, Cc, From.  Server SMTP
  systems SHOULD NOT reject messages based on perceived defects in the
  RFC 822 or MIME [12] message header or message body.  In particular,




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  they MUST NOT reject messages in which the numbers of Resent-fields
  do not match or Resent-to appears without Resent-from and/or Resent-
  date.

  Mail transaction commands MUST be used in the order discussed above.

3.4 Forwarding for Address Correction or Updating

  Forwarding support is most often required to consolidate and simplify
  addresses within, or relative to, some enterprise and less frequently
  to establish addresses to link a person's prior address with current
  one.  Silent forwarding of messages (without server notification to
  the sender), for security or non-disclosure purposes, is common in
  the contemporary Internet.

  In both the enterprise and the "new address" cases, information
  hiding (and sometimes security) considerations argue against exposure
  of the "final" address through the SMTP protocol as a side-effect of
  the forwarding activity.  This may be especially important when the
  final address may not even be reachable by the sender.  Consequently,
  the "forwarding" mechanisms described in section 3.2 of RFC 821, and
  especially the 251 (corrected destination) and 551 reply codes from
  RCPT must be evaluated carefully by implementers and, when they are
  available, by those configuring systems.

  In particular:

  *  Servers MAY forward messages when they are aware of an address
     change.  When they do so, they MAY either provide address-updating
     information with a 251 code, or may forward "silently" and return
     a 250 code.  But, if a 251 code is used, they MUST NOT assume that
     the client will actually update address information or even return
     that information to the user.

  Alternately,

  *  Servers MAY reject or bounce messages when they are not
     deliverable when addressed.  When they do so, they MAY either
     provide address-updating information with a 551 code, or may
     reject the message as undeliverable with a 550 code and no
     address-specific information.  But, if a 551 code is used, they
     MUST NOT assume that the client will actually update address
     information or even return that information to the user.

  SMTP server implementations that support the 251 and/or 551 reply
  codes are strongly encouraged to provide configuration mechanisms so
  that sites which conclude that they would undesirably disclose
  information can disable or restrict their use.



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3.5 Commands for Debugging Addresses

3.5.1 Overview

  SMTP provides commands to verify a user name or obtain the content of
  a mailing list.  This is done with the VRFY and EXPN commands, which
  have character string arguments.  Implementations SHOULD support VRFY
  and EXPN (however, see section 3.5.2 and 7.3).

  For the VRFY command, the string is a user name or a user name and
  domain (see below).  If a normal (i.e., 250) response is returned,
  the response MAY include the full name of the user and MUST include
  the mailbox of the user.  It MUST be in either of the following
  forms:

     User Name <local-part@domain>
     local-part@domain

  When a name that is the argument to VRFY could identify more than one
  mailbox, the server MAY either note the ambiguity or identify the
  alternatives.  In other words, any of the following are legitimate
  response to VRFY:

     553 User ambiguous

  or

     553- Ambiguous;  Possibilities are
     553-Joe Smith <[email protected]>
     553-Harry Smith <[email protected]>
     553 Melvin Smith <[email protected]>

  or

     553-Ambiguous;  Possibilities
     553- <[email protected]>
     553- <[email protected]>
     553 <[email protected]>

  Under normal circumstances, a client receiving a 553 reply would be
  expected to expose the result to the user.  Use of exactly the forms
  given, and the "user ambiguous" or "ambiguous" keywords, possibly
  supplemented by extended reply codes such as those described in [34],
  will facilitate automated translation into other languages as needed.
  Of course, a client that was highly automated or that was operating
  in another language than English, might choose to try to translate
  the response, to return some other indication to the user than the




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  literal text of the reply, or to take some automated action such as
  consulting a directory service for additional information before
  reporting to the user.

  For the EXPN command, the string identifies a mailing list, and the
  successful (i.e., 250) multiline response MAY include the full name
  of the users and MUST give the mailboxes on the mailing list.

  In some hosts the distinction between a mailing list and an alias for
  a single mailbox is a bit fuzzy, since a common data structure may
  hold both types of entries, and it is possible to have mailing lists
  containing only one mailbox.  If a request is made to apply VRFY to a
  mailing list, a positive response MAY be given if a message so
  addressed would be delivered to everyone on the list, otherwise an
  error SHOULD be reported (e.g., "550 That is a mailing list, not a
  user" or "252 Unable to verify members of mailing list").  If a
  request is made to expand a user name, the server MAY return a
  positive response consisting of a list containing one name, or an
  error MAY be reported (e.g., "550 That is a user name, not a mailing
  list").

  In the case of a successful multiline reply (normal for EXPN) exactly
  one mailbox is to be specified on each line of the reply.  The case
  of an ambiguous request is discussed above.

  "User name" is a fuzzy term and has been used deliberately.  An
  implementation of the VRFY or EXPN commands MUST include at least
  recognition of local mailboxes as "user names".  However, since
  current Internet practice often results in a single host handling
  mail for multiple domains, hosts, especially hosts that provide this
  functionality, SHOULD accept the "local-part@domain" form as a "user
  name"; hosts MAY also choose to recognize other strings as "user
  names".

  The case of expanding a mailbox list requires a multiline reply, such
  as:

     C: EXPN Example-People
     S: 250-Jon Postel <[email protected]>
     S: 250-Fred Fonebone <[email protected]>
     S: 250 Sam Q. Smith <[email protected]>

  or

     C: EXPN Executive-Washroom-List
     S: 550 Access Denied to You.





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  The character string arguments of the VRFY and EXPN commands cannot
  be further restricted due to the variety of implementations of the
  user name and mailbox list concepts.  On some systems it may be
  appropriate for the argument of the EXPN command to be a file name
  for a file containing a mailing list, but again there are a variety
  of file naming conventions in the Internet.  Similarly, historical
  variations in what is returned by these commands are such that the
  response SHOULD be interpreted very carefully, if at all, and SHOULD
  generally only be used for diagnostic purposes.

3.5.2 VRFY Normal Response

  When normal (2yz or 551) responses are returned from a VRFY or EXPN
  request, the reply normally includes the mailbox name, i.e.,
  "<local-part@domain>", where "domain" is a fully qualified domain
  name, MUST appear in the syntax.  In circumstances exceptional enough
  to justify violating the intent of this specification, free-form text
  MAY be returned.  In order to facilitate parsing by both computers
  and people, addresses SHOULD appear in pointed brackets.  When
  addresses, rather than free-form debugging information, are returned,
  EXPN and VRFY MUST return only valid domain addresses that are usable
  in SMTP RCPT commands.  Consequently, if an address implies delivery
  to a program or other system, the mailbox name used to reach that
  target MUST be given.  Paths (explicit source routes) MUST NOT be
  returned by VRFY or EXPN.

  Server implementations SHOULD support both VRFY and EXPN.  For
  security reasons, implementations MAY provide local installations a
  way to disable either or both of these commands through configuration
  options or the equivalent.  When these commands are supported, they
  are not required to work across relays when relaying is supported.
  Since they were both optional in RFC 821, they MUST be listed as
  service extensions in an EHLO response, if they are supported.

3.5.3 Meaning of VRFY or EXPN Success Response

  A server MUST NOT return a 250 code in response to a VRFY or EXPN
  command unless it has actually verified the address.  In particular,
  a server MUST NOT return 250 if all it has done is to verify that the
  syntax given is valid.  In that case, 502 (Command not implemented)
  or 500 (Syntax error, command unrecognized) SHOULD be returned.  As
  stated elsewhere, implementation (in the sense of actually validating
  addresses and returning information) of VRFY and EXPN are strongly
  recommended.  Hence, implementations that return 500 or 502 for VRFY
  are not in full compliance with this specification.






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  There may be circumstances where an address appears to be valid but
  cannot reasonably be verified in real time, particularly when a
  server is acting as a mail exchanger for another server or domain.
  "Apparent validity" in this case would normally involve at least
  syntax checking and might involve verification that any domains
  specified were ones to which the host expected to be able to relay
  mail.  In these situations, reply code 252 SHOULD be returned.  These
  cases parallel the discussion of RCPT verification discussed in
  section 2.1.  Similarly, the discussion in section 3.4 applies to the
  use of reply codes 251 and 551 with VRFY (and EXPN) to indicate
  addresses that are recognized but that would be forwarded or bounced
  were mail received for them.  Implementations generally SHOULD be
  more aggressive about address verification in the case of VRFY than
  in the case of RCPT, even if it takes a little longer to do so.

3.5.4 Semantics and Applications of EXPN

  EXPN is often very useful in debugging and understanding problems
  with mailing lists and multiple-target-address aliases.  Some systems
  have attempted to use source expansion of mailing lists as a means of
  eliminating duplicates.  The propagation of aliasing systems with
  mail on the Internet, for hosts (typically with MX and CNAME DNS
  records), for mailboxes (various types of local host aliases), and in
  various proxying arrangements, has made it nearly impossible for
  these strategies to work consistently, and mail systems SHOULD NOT
  attempt them.

3.6 Domains

  Only resolvable, fully-qualified, domain names (FQDNs) are permitted
  when domain names are used in SMTP.  In other words, names that can
  be resolved to MX RRs or A RRs (as discussed in section 5) are
  permitted, as are CNAME RRs whose targets can be resolved, in turn,
  to MX or A RRs.  Local nicknames or unqualified names MUST NOT be
  used.  There are two exceptions to the rule requiring FQDNs:

  -  The domain name given in the EHLO command MUST BE either a primary
     host name (a domain name that resolves to an A RR) or, if the host
     has no name, an address literal as described in section 4.1.1.1.

  -  The reserved mailbox name "postmaster" may be used in a RCPT
     command without domain qualification (see section 4.1.1.3) and
     MUST be accepted if so used.








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3.7 Relaying

  In general, the availability of Mail eXchanger records in the domain
  name system [22, 27] makes the use of explicit source routes in the
  Internet mail system unnecessary.  Many historical problems with
  their interpretation have made their use undesirable.  SMTP clients
  SHOULD NOT generate explicit source routes except under unusual
  circumstances.  SMTP servers MAY decline to act as mail relays or to
  accept addresses that specify source routes.  When route information
  is encountered, SMTP servers are also permitted to ignore the route
  information and simply send to the final destination specified as the
  last element in the route and SHOULD do so.  There has been an
  invalid practice of using names that do not appear in the DNS as
  destination names, with the senders counting on the intermediate
  hosts specified in source routing to resolve any problems.  If source
  routes are stripped, this practice will cause failures.  This is one
  of several reasons why SMTP clients MUST NOT generate invalid source
  routes or depend on serial resolution of names.

  When source routes are not used, the process described in RFC 821 for
  constructing a reverse-path from the forward-path is not applicable
  and the reverse-path at the time of delivery will simply be the
  address that appeared in the MAIL command.

  A relay SMTP server is usually the target of a DNS MX record that
  designates it, rather than the final delivery system.  The relay
  server may accept or reject the task of relaying the mail in the same
  way it accepts or rejects mail for a local user.  If it accepts the
  task, it then becomes an SMTP client, establishes a transmission
  channel to the next SMTP server specified in the DNS (according to
  the rules in section 5), and sends it the mail.  If it declines to
  relay mail to a particular address for policy reasons, a 550 response
  SHOULD be returned.

  Many mail-sending clients exist, especially in conjunction with
  facilities that receive mail via POP3 or IMAP, that have limited
  capability to support some of the requirements of this specification,
  such as the ability to queue messages for subsequent delivery
  attempts.  For these clients, it is common practice to make private
  arrangements to send all messages to a single server for processing
  and subsequent distribution.  SMTP, as specified here, is not ideally
  suited for this role, and work is underway on standardized mail
  submission protocols that might eventually supercede the current
  practices.  In any event, because these arrangements are private and
  fall outside the scope of this specification, they are not described
  here.





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  It is important to note that MX records can point to SMTP servers
  which act as gateways into other environments, not just SMTP relays
  and final delivery systems; see sections 3.8 and 5.

  If an SMTP server has accepted the task of relaying the mail and
  later finds that the destination is incorrect or that the mail cannot
  be delivered for some other reason, then it MUST construct an
  "undeliverable mail" notification message and send it to the
  originator of the undeliverable mail (as indicated by the reverse-
  path).  Formats specified for non-delivery reports by other standards
  (see, for example, [24, 25]) SHOULD be used if possible.

  This notification message must be from the SMTP server at the relay
  host or the host that first determines that delivery cannot be
  accomplished.  Of course, SMTP servers MUST NOT send notification
  messages about problems transporting notification messages.  One way
  to prevent loops in error reporting is to specify a null reverse-path
  in the MAIL command of a notification message.  When such a message
  is transmitted the reverse-path MUST be set to null (see section
  4.5.5 for additional discussion).  A MAIL command with a null
  reverse-path appears as follows:

     MAIL FROM:<>

  As discussed in section 2.4.1, a relay SMTP has no need to inspect or
  act upon the headers or body of the message data and MUST NOT do so
  except to add its own "Received:" header (section 4.4) and,
  optionally, to attempt to detect looping in the mail system (see
  section 6.2).

3.8 Mail Gatewaying

  While the relay function discussed above operates within the Internet
  SMTP transport service environment, MX records or various forms of
  explicit routing may require that an intermediate SMTP server perform
  a translation function between one transport service and another.  As
  discussed in section 2.3.8, when such a system is at the boundary
  between two transport service environments, we refer to it as a
  "gateway" or "gateway SMTP".

  Gatewaying mail between different mail environments, such as
  different mail formats and protocols, is complex and does not easily
  yield to standardization.  However, some general requirements may be
  given for a gateway between the Internet and another mail
  environment.






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3.8.1 Header Fields in Gatewaying

  Header fields MAY be rewritten when necessary as messages are
  gatewayed across mail environment boundaries.  This may involve
  inspecting the message body or interpreting the local-part of the
  destination address in spite of the prohibitions in section 2.4.1.

  Other mail systems gatewayed to the Internet often use a subset of
  RFC 822 headers or provide similar functionality with a different
  syntax, but some of these mail systems do not have an equivalent to
  the SMTP envelope.  Therefore, when a message leaves the Internet
  environment, it may be necessary to fold the SMTP envelope
  information into the message header.  A possible solution would be to
  create new header fields to carry the envelope information (e.g.,
  "X-SMTP-MAIL:"  and "X-SMTP-RCPT:"); however, this would require
  changes in mail programs in foreign environments and might risk
  disclosure of private information (see section 7.2).

3.8.2 Received Lines in Gatewaying

  When forwarding a message into or out of the Internet environment, a
  gateway MUST prepend a Received: line, but it MUST NOT alter in any
  way a Received: line that is already in the header.

  "Received:" fields of messages originating from other environments
  may not conform exactly to this specification.  However, the most
  important use of Received: lines is for debugging mail faults, and
  this debugging can be severely hampered by well-meaning gateways that
  try to "fix" a Received: line.  As another consequence of trace
  fields arising in non-SMTP environments, receiving systems MUST NOT
  reject mail based on the format of a trace field and SHOULD be
  extremely robust in the light of unexpected information or formats in
  those fields.

  The gateway SHOULD indicate the environment and protocol in the "via"
  clauses of Received field(s) that it supplies.

3.8.3 Addresses in Gatewaying

  From the Internet side, the gateway SHOULD accept all valid address
  formats in SMTP commands and in RFC 822 headers, and all valid RFC
  822 messages.  Addresses and headers generated by gateways MUST
  conform to applicable Internet standards (including this one and RFC
  822).  Gateways are, of course, subject to the same rules for
  handling source routes as those described for other SMTP systems in
  section 3.3.





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3.8.4 Other Header Fields in Gatewaying

  The gateway MUST ensure that all header fields of a message that it
  forwards into the Internet mail environment meet the requirements for
  Internet mail.  In particular, all addresses in "From:", "To:",
  "Cc:", etc., fields MUST be transformed (if necessary) to satisfy RFC
  822 syntax, MUST reference only fully-qualified domain names, and
  MUST be effective and useful for sending replies.  The translation
  algorithm used to convert mail from the Internet protocols to another
  environment's protocol SHOULD ensure that error messages from the
  foreign mail environment are delivered to the return path from the
  SMTP envelope, not to the sender listed in the "From:" field (or
  other fields) of the RFC 822 message.

3.8.5 Envelopes in Gatewaying

  Similarly, when forwarding a message from another environment into
  the Internet, the gateway SHOULD set the envelope return path in
  accordance with an error message return address, if supplied by the
  foreign environment.  If the foreign environment has no equivalent
  concept, the gateway must select and use a best approximation, with
  the message originator's address as the default of last resort.

3.9 Terminating Sessions and Connections

  An SMTP connection is terminated when the client sends a QUIT
  command.  The server responds with a positive reply code, after which
  it closes the connection.

  An SMTP server MUST NOT intentionally close the connection except:

  -  After receiving a QUIT command and responding with a 221 reply.

  -  After detecting the need to shut down the SMTP service and
     returning a 421 response code.  This response code can be issued
     after the server receives any command or, if necessary,
     asynchronously from command receipt (on the assumption that the
     client will receive it after the next command is issued).

  In particular, a server that closes connections in response to
  commands that are not understood is in violation of this
  specification.  Servers are expected to be tolerant of unknown
  commands, issuing a 500 reply and awaiting further instructions from
  the client.







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  An SMTP server which is forcibly shut down via external means SHOULD
  attempt to send a line containing a 421 response code to the SMTP
  client before exiting.  The SMTP client will normally read the 421
  response code after sending its next command.

  SMTP clients that experience a connection close, reset, or other
  communications failure due to circumstances not under their control
  (in violation of the intent of this specification but sometimes
  unavoidable) SHOULD, to maintain the robustness of the mail system,
  treat the mail transaction as if a 451 response had been received and
  act accordingly.

3.10 Mailing Lists and Aliases

  An SMTP-capable host SHOULD support both the alias and the list
  models of address expansion for multiple delivery.  When a message is
  delivered or forwarded to each address of an expanded list form, the
  return address in the envelope ("MAIL FROM:") MUST be changed to be
  the address of a person or other entity who administers the list.
  However, in this case, the message header [32] MUST be left
  unchanged; in particular, the "From" field of the message header is
  unaffected.

  An important mail facility is a mechanism for multi-destination
  delivery of a single message, by transforming (or "expanding" or
  "exploding") a pseudo-mailbox address into a list of destination
  mailbox addresses.  When a message is sent to such a pseudo-mailbox
  (sometimes called an "exploder"), copies are forwarded or
  redistributed to each mailbox in the expanded list.  Servers SHOULD
  simply utilize the addresses on the list; application of heuristics
  or other matching rules to eliminate some addresses, such as that of
  the originator, is strongly discouraged.  We classify such a pseudo-
  mailbox as an "alias" or a "list", depending upon the expansion
  rules.

3.10.1 Alias

  To expand an alias, the recipient mailer simply replaces the pseudo-
  mailbox address in the envelope with each of the expanded addresses
  in turn; the rest of the envelope and the message body are left
  unchanged.  The message is then delivered or forwarded to each
  expanded address.

3.10.2 List

  A mailing list may be said to operate by "redistribution" rather than
  by "forwarding".  To expand a list, the recipient mailer replaces the
  pseudo-mailbox address in the envelope with all of the expanded



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  addresses.  The return address in the envelope is changed so that all
  error messages generated by the final deliveries will be returned to
  a list administrator, not to the message originator, who generally
  has no control over the contents of the list and will typically find
  error messages annoying.

4. The SMTP Specifications

4.1 SMTP Commands

4.1.1 Command Semantics and Syntax

  The SMTP commands define the mail transfer or the mail system
  function requested by the user.  SMTP commands are character strings
  terminated by <CRLF>.  The commands themselves are alphabetic
  characters terminated by <SP> if parameters follow and <CRLF>
  otherwise.  (In the interest of improved interoperability, SMTP
  receivers are encouraged to tolerate trailing white space before the
  terminating <CRLF>.)  The syntax of the local part of a mailbox must
  conform to receiver site conventions and the syntax specified in
  section 4.1.2.  The SMTP commands are discussed below.  The SMTP
  replies are discussed in section 4.2.

  A mail transaction involves several data objects which are
  communicated as arguments to different commands.  The reverse-path is
  the argument of the MAIL command, the forward-path is the argument of
  the RCPT command, and the mail data is the argument of the DATA
  command.  These arguments or data objects must be transmitted and
  held pending the confirmation communicated by the end of mail data
  indication which finalizes the transaction.  The model for this is
  that distinct buffers are provided to hold the types of data objects,
  that is, there is a reverse-path buffer, a forward-path buffer, and a
  mail data buffer.  Specific commands cause information to be appended
  to a specific buffer, or cause one or more buffers to be cleared.

  Several commands (RSET, DATA, QUIT) are specified as not permitting
  parameters.  In the absence of specific extensions offered by the
  server and accepted by the client, clients MUST NOT send such
  parameters and servers SHOULD reject commands containing them as
  having invalid syntax.

4.1.1.1  Extended HELLO (EHLO) or HELLO (HELO)

  These commands are used to identify the SMTP client to the SMTP
  server.  The argument field contains the fully-qualified domain name
  of the SMTP client if one is available.  In situations in which the
  SMTP client system does not have a meaningful domain name (e.g., when
  its address is dynamically allocated and no reverse mapping record is



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  available), the client SHOULD send an address literal (see section
  4.1.3), optionally followed by information that will help to identify
  the client system.  y The SMTP server identifies itself to the SMTP
  client in the connection greeting reply and in the response to this
  command.

  A client SMTP SHOULD start an SMTP session by issuing the EHLO
  command.  If the SMTP server supports the SMTP service extensions it
  will give a successful response, a failure response, or an error
  response.  If the SMTP server, in violation of this specification,
  does not support any SMTP service extensions it will generate an
  error response.  Older client SMTP systems MAY, as discussed above,
  use HELO (as specified in RFC 821) instead of EHLO, and servers MUST
  support the HELO command and reply properly to it.  In any event, a
  client MUST issue HELO or EHLO before starting a mail transaction.

  These commands, and a "250 OK" reply to one of them, confirm that
  both the SMTP client and the SMTP server are in the initial state,
  that is, there is no transaction in progress and all state tables and
  buffers are cleared.

  Syntax:

     ehlo            = "EHLO" SP Domain CRLF
     helo            = "HELO" SP Domain CRLF

  Normally, the response to EHLO will be a multiline reply.  Each line
  of the response contains a keyword and, optionally, one or more
  parameters.  Following the normal syntax for multiline replies, these
  keyworks follow the code (250) and a hyphen for all but the last
  line, and the code and a space for the last line.  The syntax for a
  positive response, using the ABNF notation and terminal symbols of
  [8], is:

     ehlo-ok-rsp  =    ( "250"    domain [ SP ehlo-greet ] CRLF )
                  / (    "250-"   domain [ SP ehlo-greet ] CRLF
                      *( "250-"   ehlo-line                CRLF )
                         "250"    SP ehlo-line             CRLF  )

     ehlo-greet   = 1*(%d0-9 / %d11-12 / %d14-127)
                  ; string of any characters other than CR or LF

     ehlo-line    = ehlo-keyword *( SP ehlo-param )

     ehlo-keyword = (ALPHA / DIGIT) *(ALPHA / DIGIT / "-")
                  ; additional syntax of ehlo-params depends on
                  ; ehlo-keyword




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     ehlo-param   = 1*(%d33-127)
                  ; any CHAR excluding <SP> and all
                  ; control characters (US-ASCII 0-31 inclusive)

  Although EHLO keywords may be specified in upper, lower, or mixed
  case, they MUST always be recognized and processed in a case-
  insensitive manner.  This is simply an extension of practices
  specified in RFC 821 and section 2.4.1.

4.1.1.2 MAIL (MAIL)

  This command is used to initiate a mail transaction in which the mail
  data is delivered to an SMTP server which may, in turn, deliver it to
  one or more mailboxes or pass it on to another system (possibly using
  SMTP).  The argument field contains a reverse-path and may contain
  optional parameters.  In general, the MAIL command may be sent only
  when no mail transaction is in progress, see section 4.1.4.

  The reverse-path consists of the sender mailbox.  Historically, that
  mailbox might optionally have been preceded by a list of hosts, but
  that behavior is now deprecated (see appendix C).  In some types of
  reporting messages for which a reply is likely to cause a mail loop
  (for example, mail delivery and nondelivery notifications), the
  reverse-path may be null (see section 3.7).

  This command clears the reverse-path buffer, the forward-path buffer,
  and the mail data buffer; and inserts the reverse-path information
  from this command into the reverse-path buffer.

  If service extensions were negotiated, the MAIL command may also
  carry parameters associated with a particular service extension.

  Syntax:

     "MAIL FROM:" ("<>" / Reverse-Path)
                      [SP Mail-parameters] CRLF

4.1.1.3 RECIPIENT (RCPT)

  This command is used to identify an individual recipient of the mail
  data; multiple recipients are specified by multiple use of this
  command.  The argument field contains a forward-path and may contain
  optional parameters.

  The forward-path normally consists of the required destination
  mailbox.  Sending systems SHOULD not generate the optional list of
  hosts known as a source route.  Receiving systems MUST recognize




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  source route syntax but SHOULD strip off the source route
  specification and utilize the domain name associated with the mailbox
  as if the source route had not been provided.

  Similarly, relay hosts SHOULD strip or ignore source routes, and
  names MUST NOT be copied into the reverse-path.  When mail reaches
  its ultimate destination (the forward-path contains only a
  destination mailbox), the SMTP server inserts it into the destination
  mailbox in accordance with its host mail conventions.

  For example, mail received at relay host xyz.com with envelope
  commands

     MAIL FROM:<[email protected]>
     RCPT TO:<@hosta.int,@jkl.org:[email protected]>

  will normally be sent directly on to host d.bar.org with envelope
  commands

     MAIL FROM:<[email protected]>
     RCPT TO:<[email protected]>

  As provided in appendix C, xyz.com MAY also choose to relay the
  message to hosta.int, using the envelope commands

     MAIL FROM:<[email protected]>
     RCPT TO:<@hosta.int,@jkl.org:[email protected]>

  or to jkl.org, using the envelope commands

     MAIL FROM:<[email protected]>
     RCPT TO:<@jkl.org:[email protected]>

  Of course, since hosts are not required to relay mail at all, xyz.com
  may also reject the message entirely when the RCPT command is
  received, using a 550 code (since this is a "policy reason").

  If service extensions were negotiated, the RCPT command may also
  carry parameters associated with a particular service extension
  offered by the server.  The client MUST NOT transmit parameters other
  than those associated with a service extension offered by the server
  in its EHLO response.

Syntax:
  "RCPT TO:" ("<Postmaster@" domain ">" / "<Postmaster>" / Forward-Path)
                   [SP Rcpt-parameters] CRLF





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4.1.1.4 DATA (DATA)

  The receiver normally sends a 354 response to DATA, and then treats
  the lines (strings ending in <CRLF> sequences, as described in
  section 2.3.7) following the command as mail data from the sender.
  This command causes the mail data to be appended to the mail data
  buffer.  The mail data may contain any of the 128 ASCII character
  codes, although experience has indicated that use of control
  characters other than SP, HT, CR, and LF may cause problems and
  SHOULD be avoided when possible.

  The mail data is terminated by a line containing only a period, that
  is, the character sequence "<CRLF>.<CRLF>" (see section 4.5.2).  This
  is the end of mail data indication.  Note that the first <CRLF> of
  this terminating sequence is also the <CRLF> that ends the final line
  of the data (message text) or, if there was no data, ends the DATA
  command itself.  An extra <CRLF> MUST NOT be added, as that would
  cause an empty line to be added to the message.  The only exception
  to this rule would arise if the message body were passed to the
  originating SMTP-sender with a final "line" that did not end in
  <CRLF>; in that case, the originating SMTP system MUST either reject
  the message as invalid or add <CRLF> in order to have the receiving
  SMTP server recognize the "end of data" condition.

  The custom of accepting lines ending only in <LF>, as a concession to
  non-conforming behavior on the part of some UNIX systems, has proven
  to cause more interoperability problems than it solves, and SMTP
  server systems MUST NOT do this, even in the name of improved
  robustness.  In particular, the sequence "<LF>.<LF>" (bare line
  feeds, without carriage returns) MUST NOT be treated as equivalent to
  <CRLF>.<CRLF> as the end of mail data indication.

  Receipt of the end of mail data indication requires the server to
  process the stored mail transaction information.  This processing
  consumes the information in the reverse-path buffer, the forward-path
  buffer, and the mail data buffer, and on the completion of this
  command these buffers are cleared.  If the processing is successful,
  the receiver MUST send an OK reply.  If the processing fails the
  receiver MUST send a failure reply.  The SMTP model does not allow
  for partial failures at this point: either the message is accepted by
  the server for delivery and a positive response is returned or it is
  not accepted and a failure reply is returned.  In sending a positive
  completion reply to the end of data indication, the receiver takes
  full responsibility for the message (see section 6.1).  Errors that
  are diagnosed subsequently MUST be reported in a mail message, as
  discussed in section 4.4.





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  When the SMTP server accepts a message either for relaying or for
  final delivery, it inserts a trace record (also referred to
  interchangeably as a "time stamp line" or "Received" line) at the top
  of the mail data.  This trace record indicates the identity of the
  host that sent the message, the identity of the host that received
  the message (and is inserting this time stamp), and the date and time
  the message was received.  Relayed messages will have multiple time
  stamp lines.  Details for formation of these lines, including their
  syntax, is specified in section 4.4.

  Additional discussion about the operation of the DATA command appears
  in section 3.3.

  Syntax:
     "DATA" CRLF

4.1.1.5 RESET (RSET)

  This command specifies that the current mail transaction will be
  aborted.  Any stored sender, recipients, and mail data MUST be
  discarded, and all buffers and state tables cleared.  The receiver
  MUST send a "250 OK" reply to a RSET command with no arguments.  A
  reset command may be issued by the client at any time.  It is
  effectively equivalent to a NOOP (i.e., if has no effect) if issued
  immediately after EHLO, before EHLO is issued in the session, after
  an end-of-data indicator has been sent and acknowledged, or
  immediately before a QUIT.  An SMTP server MUST NOT close the
  connection as the result of receiving a RSET; that action is reserved
  for QUIT (see section 4.1.1.10).

  Since EHLO implies some additional processing and response by the
  server, RSET will normally be more efficient than reissuing that
  command, even though the formal semantics are the same.

  There are circumstances, contrary to the intent of this
  specification, in which an SMTP server may receive an indication that
  the underlying TCP connection has been closed or reset.  To preserve
  the robustness of the mail system, SMTP servers SHOULD be prepared
  for this condition and SHOULD treat it as if a QUIT had been received
  before the connection disappeared.

  Syntax:
     "RSET" CRLF








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4.1.1.6 VERIFY (VRFY)

  This command asks the receiver to confirm that the argument
  identifies a user or mailbox.  If it is a user name, information is
  returned as specified in section 3.5.

  This command has no effect on the reverse-path buffer, the forward-
  path buffer, or the mail data buffer.

  Syntax:
     "VRFY" SP String CRLF

4.1.1.7 EXPAND (EXPN)

  This command asks the receiver to confirm that the argument
  identifies a mailing list, and if so, to return the membership of
  that list.  If the command is successful, a reply is returned
  containing information as described in section 3.5.  This reply will
  have multiple lines except in the trivial case of a one-member list.

  This command has no effect on the reverse-path buffer, the forward-
  path buffer, or the mail data buffer and may be issued at any time.

  Syntax:
     "EXPN" SP String CRLF

4.1.1.8 HELP (HELP)

  This command causes the server to send helpful information to the
  client.  The command MAY take an argument (e.g., any command name)
  and return more specific information as a response.

  This command has no effect on the reverse-path buffer, the forward-
  path buffer, or the mail data buffer and may be issued at any time.

  SMTP servers SHOULD support HELP without arguments and MAY support it
  with arguments.

  Syntax:
     "HELP" [ SP String ] CRLF

4.1.1.9 NOOP (NOOP)

  This command does not affect any parameters or previously entered
  commands.  It specifies no action other than that the receiver send
  an OK reply.





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  This command has no effect on the reverse-path buffer, the forward-
  path buffer, or the mail data buffer and may be issued at any time.
  If a parameter string is specified, servers SHOULD ignore it.

  Syntax:
     "NOOP" [ SP String ] CRLF

4.1.1.10 QUIT (QUIT)

  This command specifies that the receiver MUST send an OK reply, and
  then close the transmission channel.

  The receiver MUST NOT intentionally close the transmission channel
  until it receives and replies to a QUIT command (even if there was an
  error).  The sender MUST NOT intentionally close the transmission
  channel until it sends a QUIT command and SHOULD wait until it
  receives the reply (even if there was an error response to a previous
  command).  If the connection is closed prematurely due to violations
  of the above or system or network failure, the server MUST cancel any
  pending transaction, but not undo any previously completed
  transaction, and generally MUST act as if the command or transaction
  in progress had received a temporary error (i.e., a 4yz response).

  The QUIT command may be issued at any time.

  Syntax:
     "QUIT" CRLF

4.1.2 Command Argument Syntax

  The syntax of the argument fields of the above commands (using the
  syntax specified in [8] where applicable) is given below.  Some of
  the productions given below are used only in conjunction with source
  routes as described in appendix C.  Terminals not defined in this
  document, such as ALPHA, DIGIT, SP, CR, LF, CRLF, are as defined in
  the "core" syntax [8 (section 6)] or in the message format syntax
  [32].

     Reverse-path = Path
     Forward-path = Path
     Path = "<" [ A-d-l ":" ] Mailbox ">"
     A-d-l = At-domain *( "," A-d-l )
           ; Note that this form, the so-called "source route",
           ; MUST BE accepted, SHOULD NOT be generated, and SHOULD be
           ; ignored.
     At-domain = "@" domain
     Mail-parameters = esmtp-param *(SP esmtp-param)
     Rcpt-parameters = esmtp-param *(SP esmtp-param)



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     esmtp-param     = esmtp-keyword ["=" esmtp-value]
     esmtp-keyword   = (ALPHA / DIGIT) *(ALPHA / DIGIT / "-")
     esmtp-value     = 1*(%d33-60 / %d62-127)
           ; any CHAR excluding "=", SP, and control characters
     Keyword  = Ldh-str
     Argument = Atom
     Domain = (sub-domain 1*("." sub-domain)) / address-literal
     sub-domain = Let-dig [Ldh-str]

     address-literal = "[" IPv4-address-literal /
                           IPv6-address-literal /
                           General-address-literal "]"
           ; See section 4.1.3

     Mailbox = Local-part "@" Domain

     Local-part = Dot-string / Quoted-string
           ; MAY be case-sensitive

     Dot-string = Atom *("." Atom)

     Atom = 1*atext

     Quoted-string = DQUOTE *qcontent DQUOTE

     String = Atom / Quoted-string

  While the above definition for Local-part is relatively permissive,
  for maximum interoperability, a host that expects to receive mail
  SHOULD avoid defining mailboxes where the Local-part requires (or
  uses) the Quoted-string form or where the Local-part is case-
  sensitive.  For any purposes that require generating or comparing
  Local-parts (e.g., to specific mailbox names), all quoted forms MUST
  be treated as equivalent and the sending system SHOULD transmit the
  form that uses the minimum quoting possible.

  Systems MUST NOT define mailboxes in such a way as to require the use
  in SMTP of non-ASCII characters (octets with the high order bit set
  to one) or ASCII "control characters" (decimal value 0-31 and 127).
  These characters MUST NOT be used in MAIL or RCPT commands or other
  commands that require mailbox names.

  Note that the backslash, "\", is a quote character, which is used to
  indicate that the next character is to be used literally (instead of
  its normal interpretation).  For example, "Joe\,Smith" indicates a
  single nine character user field with the comma being the fourth
  character of the field.




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  To promote interoperability and consistent with long-standing
  guidance about conservative use of the DNS in naming and applications
  (e.g., see section 2.3.1 of the base DNS document, RFC1035 [22]),
  characters outside the set of alphas, digits, and hyphen MUST NOT
  appear in domain name labels for SMTP clients or servers.  In
  particular, the underscore character is not permitted.  SMTP servers
  that receive a command in which invalid character codes have been
  employed, and for which there are no other reasons for rejection,
  MUST reject that command with a 501 response.

4.1.3 Address Literals

  Sometimes a host is not known to the domain name system and
  communication (and, in particular, communication to report and repair
  the error) is blocked.  To bypass this barrier a special literal form
  of the address is allowed as an alternative to a domain name.  For
  IPv4 addresses, this form uses four small decimal integers separated
  by dots and enclosed by brackets such as [123.255.37.2], which
  indicates an (IPv4) Internet Address in sequence-of-octets form.  For
  IPv6 and other forms of addressing that might eventually be
  standardized, the form consists of a standardized "tag" that
  identifies the address syntax, a colon, and the address itself, in a
  format specified as part of the IPv6 standards [17].

  Specifically:

     IPv4-address-literal = Snum 3("." Snum)
     IPv6-address-literal = "IPv6:" IPv6-addr
     General-address-literal = Standardized-tag ":" 1*dcontent
     Standardized-tag = Ldh-str
           ; MUST be specified in a standards-track RFC
           ; and registered with IANA

     Snum = 1*3DIGIT  ; representing a decimal integer
           ; value in the range 0 through 255
     Let-dig = ALPHA / DIGIT
     Ldh-str = *( ALPHA / DIGIT / "-" ) Let-dig

     IPv6-addr = IPv6-full / IPv6-comp / IPv6v4-full / IPv6v4-comp
     IPv6-hex  = 1*4HEXDIG
     IPv6-full = IPv6-hex 7(":" IPv6-hex)
     IPv6-comp = [IPv6-hex *5(":" IPv6-hex)] "::" [IPv6-hex *5(":"
                IPv6-hex)]
           ; The "::" represents at least 2 16-bit groups of zeros
           ; No more than 6 groups in addition to the "::" may be
           ; present
     IPv6v4-full = IPv6-hex 5(":" IPv6-hex) ":" IPv4-address-literal
     IPv6v4-comp = [IPv6-hex *3(":" IPv6-hex)] "::"



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RFC 2821             Simple Mail Transfer Protocol            April 2001


                  [IPv6-hex *3(":" IPv6-hex) ":"] IPv4-address-literal
           ; The "::" represents at least 2 16-bit groups of zeros
           ; No more than 4 groups in addition to the "::" and
           ; IPv4-address-literal may be present

4.1.4 Order of Commands

  There are restrictions on the order in which these commands may be
  used.

  A session that will contain mail transactions MUST first be
  initialized by the use of the EHLO command.  An SMTP server SHOULD
  accept commands for non-mail transactions (e.g., VRFY or EXPN)
  without this initialization.

  An EHLO command MAY be issued by a client later in the session.  If
  it is issued after the session begins, the SMTP server MUST clear all
  buffers and reset the state exactly as if a RSET command had been
  issued.  In other words, the sequence of RSET followed immediately by
  EHLO is redundant, but not harmful other than in the performance cost
  of executing unnecessary commands.

  If the EHLO command is not acceptable to the SMTP server, 501, 500,
  or 502 failure replies MUST be returned as appropriate.  The SMTP
  server MUST stay in the same state after transmitting these replies
  that it was in before the EHLO was received.

  The SMTP client MUST, if possible, ensure that the domain parameter
  to the EHLO command is a valid principal host name (not a CNAME or MX
  name) for its host.  If this is not possible (e.g., when the client's
  address is dynamically assigned and the client does not have an
  obvious name), an address literal SHOULD be substituted for the
  domain name and supplemental information provided that will assist in
  identifying the client.

  An SMTP server MAY verify that the domain name parameter in the EHLO
  command actually corresponds to the IP address of the client.
  However, the server MUST NOT refuse to accept a message for this
  reason if the verification fails: the information about verification
  failure is for logging and tracing only.

  The NOOP, HELP, EXPN, VRFY, and RSET commands can be used at any time
  during a session, or without previously initializing a session.  SMTP
  servers SHOULD process these normally (that is, not return a 503
  code) even if no EHLO command has yet been received; clients SHOULD
  open a session with EHLO before sending these commands.





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  If these rules are followed, the example in RFC 821 that shows "550
  access denied to you" in response to an EXPN command is incorrect
  unless an EHLO command precedes the EXPN or the denial of access is
  based on the client's IP address or other authentication or
  authorization-determining mechanisms.

  The MAIL command (or the obsolete SEND, SOML, or SAML commands)
  begins a mail transaction.  Once started, a mail transaction consists
  of a transaction beginning command, one or more RCPT commands, and a
  DATA command, in that order.  A mail transaction may be aborted by
  the RSET (or a new EHLO) command.  There may be zero or more
  transactions in a session.  MAIL (or SEND, SOML, or SAML) MUST NOT be
  sent if a mail transaction is already open, i.e., it should be sent
  only if no mail transaction had been started in the session, or it
  the previous one successfully concluded with a successful DATA
  command, or if the previous one was aborted with a RSET.

  If the transaction beginning command argument is not acceptable, a
  501 failure reply MUST be returned and the SMTP server MUST stay in
  the same state.  If the commands in a transaction are out of order to
  the degree that they cannot be processed by the server, a 503 failure
  reply MUST be returned and the SMTP server MUST stay in the same
  state.

  The last command in a session MUST be the QUIT command.  The QUIT
  command cannot be used at any other time in a session, but SHOULD be
  used by the client SMTP to request connection closure, even when no
  session opening command was sent and accepted.

4.1.5 Private-use Commands

  As specified in section 2.2.2, commands starting in "X" may be used
  by bilateral agreement between the client (sending) and server
  (receiving) SMTP agents.  An SMTP server that does not recognize such
  a command is expected to reply with "500 Command not recognized".  An
  extended SMTP server MAY list the feature names associated with these
  private commands in the response to the EHLO command.

  Commands sent or accepted by SMTP systems that do not start with "X"
  MUST conform to the requirements of section 2.2.2.

4.2 SMTP Replies

  Replies to SMTP commands serve to ensure the synchronization of
  requests and actions in the process of mail transfer and to guarantee
  that the SMTP client always knows the state of the SMTP server.
  Every command MUST generate exactly one reply.




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RFC 2821             Simple Mail Transfer Protocol            April 2001


  The details of the command-reply sequence are described in section
  4.3.

  An SMTP reply consists of a three digit number (transmitted as three
  numeric characters) followed by some text unless specified otherwise
  in this document.  The number is for use by automata to determine
  what state to enter next; the text is for the human user.  The three
  digits contain enough encoded information that the SMTP client need
  not examine the text and may either discard it or pass it on to the
  user, as appropriate.  Exceptions are as noted elsewhere in this
  document.  In particular, the 220, 221, 251, 421, and 551 reply codes
  are associated with message text that must be parsed and interpreted
  by machines.  In the general case, the text may be receiver dependent
  and context dependent, so there are likely to be varying texts for
  each reply code.  A discussion of the theory of reply codes is given
  in section 4.2.1.  Formally, a reply is defined to be the sequence: a
  three-digit code, <SP>, one line of text, and <CRLF>, or a multiline
  reply (as defined in section 4.2.1).  Since, in violation of this
  specification, the text is sometimes not sent, clients which do not
  receive it SHOULD be prepared to process the code alone (with or
  without a trailing space character).  Only the EHLO, EXPN, and HELP
  commands are expected to result in multiline replies in normal
  circumstances, however, multiline replies are allowed for any
  command.

  In ABNF, server responses are:

     Greeting = "220 " Domain [ SP text ] CRLF
     Reply-line = Reply-code [ SP text ] CRLF

  where "Greeting" appears only in the 220 response that announces that
  the server is opening its part of the connection.

  An SMTP server SHOULD send only the reply codes listed in this
  document.  An SMTP server SHOULD use the text shown in the examples
  whenever appropriate.

  An SMTP client MUST determine its actions only by the reply code, not
  by the text (except for the "change of address" 251 and 551 and, if
  necessary, 220, 221, and 421 replies); in the general case, any text,
  including no text at all (although senders SHOULD NOT send bare
  codes), MUST be acceptable.  The space (blank) following the reply
  code is considered part of the text.  Whenever possible, a receiver-
  SMTP SHOULD test the first digit (severity indication) of the reply
  code.






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RFC 2821             Simple Mail Transfer Protocol            April 2001


  The list of codes that appears below MUST NOT be construed as
  permanent.  While the addition of new codes should be a rare and
  significant activity, with supplemental information in the textual
  part of the response being preferred, new codes may be added as the
  result of new Standards or Standards-track specifications.
  Consequently, a sender-SMTP MUST be prepared to handle codes not
  specified in this document and MUST do so by interpreting the first
  digit only.

4.2.1 Reply Code Severities and Theory

  The three digits of the reply each have a special significance.  The
  first digit denotes whether the response is good, bad or incomplete.
  An unsophisticated SMTP client, or one that receives an unexpected
  code, will be able to determine its next action (proceed as planned,
  redo, retrench, etc.) by examining this first digit.  An SMTP client
  that wants to know approximately what kind of error occurred (e.g.,
  mail system error, command syntax error) may examine the second
  digit.  The third digit and any supplemental information that may be
  present is reserved for the finest gradation of information.

  There are five values for the first digit of the reply code:

  1yz   Positive Preliminary reply
     The command has been accepted, but the requested action is being
     held in abeyance, pending confirmation of the information in this
     reply.  The SMTP client should send another command specifying
     whether to continue or abort the action.  Note: unextended SMTP
     does not have any commands that allow this type of reply, and so
     does not have continue or abort commands.

  2yz   Positive Completion reply
     The requested action has been successfully completed.  A new
     request may be initiated.

  3yz   Positive Intermediate reply
     The command has been accepted, but the requested action is being
     held in abeyance, pending receipt of further information.  The
     SMTP client should send another command specifying this
     information.  This reply is used in command sequence groups (i.e.,
     in DATA).

  4yz   Transient Negative Completion reply
     The command was not accepted, and the requested action did not
     occur.  However, the error condition is temporary and the action
     may be requested again.  The sender should return to the beginning
     of the command sequence (if any).  It is difficult to assign a
     meaning to "transient" when two different sites (receiver- and



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RFC 2821             Simple Mail Transfer Protocol            April 2001


     sender-SMTP agents) must agree on the interpretation.  Each reply
     in this category might have a different time value, but the SMTP
     client is encouraged to try again.  A rule of thumb to determine
     whether a reply fits into the 4yz or the 5yz category (see below)
     is that replies are 4yz if they can be successful if repeated
     without any change in command form or in properties of the sender
     or receiver (that is, the command is repeated identically and the
     receiver does not put up a new implementation.)

  5yz   Permanent Negative Completion reply
     The command was not accepted and the requested action did not
     occur.  The SMTP client is discouraged from repeating the exact
     request (in the same sequence).  Even some "permanent" error
     conditions can be corrected, so the human user may want to direct
     the SMTP client to reinitiate the command sequence by direct
     action at some point in the future (e.g., after the spelling has
     been changed, or the user has altered the account status).

  The second digit encodes responses in specific categories:

  x0z   Syntax: These replies refer to syntax errors, syntactically
     correct commands that do not fit any functional category, and
     unimplemented or superfluous commands.

  x1z   Information:  These are replies to requests for information,
     such as status or help.

  x2z   Connections: These are replies referring to the transmission
     channel.

  x3z   Unspecified.

  x4z   Unspecified.

  x5z   Mail system: These replies indicate the status of the receiver
     mail system vis-a-vis the requested transfer or other mail system
     action.

  The third digit gives a finer gradation of meaning in each category
  specified by the second digit.  The list of replies illustrates this.
  Each reply text is recommended rather than mandatory, and may even
  change according to the command with which it is associated.  On the
  other hand, the reply codes must strictly follow the specifications
  in this section.  Receiver implementations should not invent new
  codes for slightly different situations from the ones described here,
  but rather adapt codes already defined.





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RFC 2821             Simple Mail Transfer Protocol            April 2001


  For example, a command such as NOOP, whose successful execution does
  not offer the SMTP client any new information, will return a 250
  reply.  The reply is 502 when the command requests an unimplemented
  non-site-specific action.  A refinement of that is the 504 reply for
  a command that is implemented, but that requests an unimplemented
  parameter.

  The reply text may be longer than a single line; in these cases the
  complete text must be marked so the SMTP client knows when it can
  stop reading the reply.  This requires a special format to indicate a
  multiple line reply.

  The format for multiline replies requires that every line, except the
  last, begin with the reply code, followed immediately by a hyphen,
  "-" (also known as minus), followed by text.  The last line will
  begin with the reply code, followed immediately by <SP>, optionally
  some text, and <CRLF>.  As noted above, servers SHOULD send the <SP>
  if subsequent text is not sent, but clients MUST be prepared for it
  to be omitted.

  For example:

     123-First line
     123-Second line
     123-234 text beginning with numbers
     123 The last line

  In many cases the SMTP client then simply needs to search for a line
  beginning with the reply code followed by <SP> or <CRLF> and ignore
  all preceding lines.  In a few cases, there is important data for the
  client in the reply "text".  The client will be able to identify
  these cases from the current context.

4.2.2 Reply Codes by Function Groups

     500 Syntax error, command unrecognized
        (This may include errors such as command line too long)
     501 Syntax error in parameters or arguments
     502 Command not implemented  (see section 4.2.4)
     503 Bad sequence of commands
     504 Command parameter not implemented

     211 System status, or system help reply
     214 Help message
        (Information on how to use the receiver or the meaning of a
        particular non-standard command; this reply is useful only
        to the human user)




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RFC 2821             Simple Mail Transfer Protocol            April 2001


     220 <domain> Service ready
     221 <domain> Service closing transmission channel
     421 <domain> Service not available, closing transmission channel
        (This may be a reply to any command if the service knows it
        must shut down)

     250 Requested mail action okay, completed
     251 User not local; will forward to <forward-path>
        (See section 3.4)
     252 Cannot VRFY user, but will accept message and attempt
         delivery
        (See section 3.5.3)
     450 Requested mail action not taken: mailbox unavailable
        (e.g., mailbox busy)
     550 Requested action not taken: mailbox unavailable
        (e.g., mailbox not found, no access, or command rejected
        for policy reasons)
     451 Requested action aborted: error in processing
     551 User not local; please try <forward-path>
        (See section 3.4)
     452 Requested action not taken: insufficient system storage
     552 Requested mail action aborted: exceeded storage allocation
     553 Requested action not taken: mailbox name not allowed
        (e.g., mailbox syntax incorrect)
     354 Start mail input; end with <CRLF>.<CRLF>
     554 Transaction failed (Or, in the case of a connection-opening
         response, "No SMTP service here")

4.2.3  Reply Codes in Numeric Order

     211 System status, or system help reply
     214 Help message
        (Information on how to use the receiver or the meaning of a
        particular non-standard command; this reply is useful only
        to the human user)
     220 <domain> Service ready
     221 <domain> Service closing transmission channel
     250 Requested mail action okay, completed
     251 User not local; will forward to <forward-path>
        (See section 3.4)
     252 Cannot VRFY user, but will accept message and attempt
        delivery
        (See section 3.5.3)

     354 Start mail input; end with <CRLF>.<CRLF>






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RFC 2821             Simple Mail Transfer Protocol            April 2001


     421 <domain> Service not available, closing transmission channel
        (This may be a reply to any command if the service knows it
        must shut down)
     450 Requested mail action not taken: mailbox unavailable
        (e.g., mailbox busy)
     451 Requested action aborted: local error in processing
     452 Requested action not taken: insufficient system storage
     500 Syntax error, command unrecognized
        (This may include errors such as command line too long)
     501 Syntax error in parameters or arguments
     502 Command not implemented (see section 4.2.4)
     503 Bad sequence of commands
     504 Command parameter not implemented
     550 Requested action not taken: mailbox unavailable
        (e.g., mailbox not found, no access, or command rejected
        for policy reasons)
     551 User not local; please try <forward-path>
        (See section 3.4)
     552 Requested mail action aborted: exceeded storage allocation
     553 Requested action not taken: mailbox name not allowed
        (e.g., mailbox syntax incorrect)
     554 Transaction failed  (Or, in the case of a connection-opening
         response, "No SMTP service here")

4.2.4 Reply Code 502

  Questions have been raised as to when reply code 502 (Command not
  implemented) SHOULD be returned in preference to other codes.  502
  SHOULD be used when the command is actually recognized by the SMTP
  server, but not implemented.  If the command is not recognized, code
  500 SHOULD be returned.  Extended SMTP systems MUST NOT list
  capabilities in response to EHLO for which they will return 502 (or
  500) replies.

4.2.5 Reply Codes After DATA and the Subsequent <CRLF>.<CRLF>

  When an SMTP server returns a positive completion status (2yz code)
  after the DATA command is completed with <CRLF>.<CRLF>, it accepts
  responsibility for:

  -  delivering the message (if the recipient mailbox exists), or

  -  if attempts to deliver the message fail due to transient
     conditions, retrying delivery some reasonable number of times at
     intervals as specified in section 4.5.4.






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RFC 2821             Simple Mail Transfer Protocol            April 2001


  -  if attempts to deliver the message fail due to permanent
     conditions, or if repeated attempts to deliver the message fail
     due to transient conditions, returning appropriate notification to
     the sender of the original message (using the address in the SMTP
     MAIL command).

  When an SMTP server returns a permanent error status (5yz) code after
  the DATA command is completed with <CRLF>.<CRLF>, it MUST NOT make
  any subsequent attempt to deliver that message.  The SMTP client
  retains responsibility for delivery of that message and may either
  return it to the user or requeue it for a subsequent attempt (see
  section 4.5.4.1).

  The user who originated the message SHOULD be able to interpret the
  return of a transient failure status (by mail message or otherwise)
  as a non-delivery indication, just as a permanent failure would be
  interpreted.  I.e., if the client SMTP successfully handles these
  conditions, the user will not receive such a reply.

  When an SMTP server returns a permanent error status (5yz) code after
  the DATA command is completely with <CRLF>.<CRLF>, it MUST NOT make
  any subsequent attempt to deliver the message.  As with temporary
  error status codes, the SMTP client retains responsibility for the
  message, but SHOULD not again attempt delivery to the same server
  without user review and intervention of the message.

4.3 Sequencing of Commands and Replies

4.3.1 Sequencing Overview

  The communication between the sender and receiver is an alternating
  dialogue, controlled by the sender.  As such, the sender issues a
  command and the receiver responds with a reply.  Unless other
  arrangements are negotiated through service extensions, the sender
  MUST wait for this response before sending further commands.

  One important reply is the connection greeting.  Normally, a receiver
  will send a 220 "Service ready" reply when the connection is
  completed.  The sender SHOULD wait for this greeting message before
  sending any commands.

  Note: all the greeting-type replies have the official name (the
  fully-qualified primary domain name) of the server host as the first
  word following the reply code.  Sometimes the host will have no
  meaningful name.  See 4.1.3 for a discussion of alternatives in these
  situations.





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  For example,

     220 ISIF.USC.EDU Service ready
  or
     220 mail.foo.com SuperSMTP v 6.1.2 Service ready
  or
     220 [10.0.0.1] Clueless host service ready

  The table below lists alternative success and failure replies for
  each command.  These SHOULD be strictly adhered to: a receiver may
  substitute text in the replies, but the meaning and action implied by
  the code numbers and by the specific command reply sequence cannot be
  altered.

4.3.2 Command-Reply Sequences

  Each command is listed with its usual possible replies.  The prefixes
  used before the possible replies are "I" for intermediate, "S" for
  success, and "E" for error.  Since some servers may generate other
  replies under special circumstances, and to allow for future
  extension, SMTP clients SHOULD, when possible, interpret only the
  first digit of the reply and MUST be prepared to deal with
  unrecognized reply codes by interpreting the first digit only.
  Unless extended using the mechanisms described in section 2.2, SMTP
  servers MUST NOT transmit reply codes to an SMTP client that are
  other than three digits or that do not start in a digit between 2 and
  5 inclusive.

  These sequencing rules and, in principle, the codes themselves, can
  be extended or modified by SMTP extensions offered by the server and
  accepted (requested) by the client.

  In addition to the codes listed below, any SMTP command can return
  any of the following codes if the corresponding unusual circumstances
  are encountered:

  500  For the "command line too long" case or if the command name was
     not recognized.  Note that producing a "command not recognized"
     error in response to the required subset of these commands is a
     violation of this specification.

  501  Syntax error in command or arguments.  In order to provide for
     future extensions, commands that are specified in this document as
     not accepting arguments (DATA, RSET, QUIT) SHOULD return a 501
     message if arguments are supplied in the absence of EHLO-
     advertised extensions.

  421  Service shutting down and closing transmission channel



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  Specific sequences are:

  CONNECTION ESTABLISHMENT
     S: 220
     E: 554
  EHLO or HELO
     S: 250
     E: 504, 550
  MAIL
     S: 250
     E: 552, 451, 452, 550, 553, 503
  RCPT
     S: 250, 251 (but see section 3.4 for discussion of 251 and 551)
     E: 550, 551, 552, 553, 450, 451, 452, 503, 550
  DATA
     I: 354 -> data -> S: 250
                       E: 552, 554, 451, 452
     E: 451, 554, 503
  RSET
     S: 250
  VRFY
     S: 250, 251, 252
     E: 550, 551, 553, 502, 504
  EXPN
     S: 250, 252
     E: 550, 500, 502, 504
  HELP
     S: 211, 214
     E: 502, 504
  NOOP
     S: 250
  QUIT
     S: 221

4.4 Trace Information

  When an SMTP server receives a message for delivery or further
  processing, it MUST insert trace ("time stamp" or "Received")
  information at the beginning of the message content, as discussed in
  section 4.1.1.4.

  This line MUST be structured as follows:

  -  The FROM field, which MUST be supplied in an SMTP environment,
     SHOULD contain both (1) the name of the source host as presented
     in the EHLO command and (2) an address literal containing the IP
     address of the source, determined from the TCP connection.




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  -  The ID field MAY contain an "@" as suggested in RFC 822, but this
     is not required.

  -  The FOR field MAY contain a list of <path> entries when multiple
     RCPT commands have been given.  This may raise some security
     issues and is usually not desirable; see section 7.2.

  An Internet mail program MUST NOT change a Received: line that was
  previously added to the message header.  SMTP servers MUST prepend
  Received lines to messages; they MUST NOT change the order of
  existing lines or insert Received lines in any other location.

  As the Internet grows, comparability of Received fields is important
  for detecting problems, especially slow relays.  SMTP servers that
  create Received fields SHOULD use explicit offsets in the dates
  (e.g., -0800), rather than time zone names of any type.  Local time
  (with an offset) is preferred to UT when feasible.  This formulation
  allows slightly more information about local circumstances to be
  specified.  If UT is needed, the receiver need merely do some simple
  arithmetic to convert the values.  Use of UT loses information about
  the time zone-location of the server.  If it is desired to supply a
  time zone name, it SHOULD be included in a comment.

  When the delivery SMTP server makes the "final delivery" of a
  message, it inserts a return-path line at the beginning of the mail
  data.  This use of return-path is required; mail systems MUST support
  it.  The return-path line preserves the information in the <reverse-
  path> from the MAIL command.  Here, final delivery means the message
  has left the SMTP environment.  Normally, this would mean it had been
  delivered to the destination user or an associated mail drop, but in
  some cases it may be further processed and transmitted by another
  mail system.

  It is possible for the mailbox in the return path to be different
  from the actual sender's mailbox, for example, if error responses are
  to be delivered to a special error handling mailbox rather than to
  the message sender.  When mailing lists are involved, this
  arrangement is common and useful as a means of directing errors to
  the list maintainer rather than the message originator.

  The text above implies that the final mail data will begin with a
  return path line, followed by one or more time stamp lines.  These
  lines will be followed by the mail data headers and body [32].

  It is sometimes difficult for an SMTP server to determine whether or
  not it is making final delivery since forwarding or other operations
  may occur after the message is accepted for delivery.  Consequently,




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  any further (forwarding, gateway, or relay) systems MAY remove the
  return path and rebuild the MAIL command as needed to ensure that
  exactly one such line appears in a delivered message.

  A message-originating SMTP system SHOULD NOT send a message that
  already contains a Return-path header.  SMTP servers performing a
  relay function MUST NOT inspect the message data, and especially not
  to the extent needed to determine if Return-path headers are present.
  SMTP servers making final delivery MAY remove Return-path headers
  before adding their own.

  The primary purpose of the Return-path is to designate the address to
  which messages indicating non-delivery or other mail system failures
  are to be sent.  For this to be unambiguous, exactly one return path
  SHOULD be present when the message is delivered.  Systems using RFC
  822 syntax with non-SMTP transports SHOULD designate an unambiguous
  address, associated with the transport envelope, to which error
  reports (e.g., non-delivery messages) should be sent.

  Historical note: Text in RFC 822 that appears to contradict the use
  of the Return-path header (or the envelope reverse path address from
  the MAIL command) as the destination for error messages is not
  applicable on the Internet.  The reverse path address (as copied into
  the Return-path) MUST be used as the target of any mail containing
  delivery error messages.

  In particular:

  -  a gateway from SMTP->elsewhere SHOULD insert a return-path header,
     unless it is known that the "elsewhere" transport also uses
     Internet domain addresses and maintains the envelope sender
     address separately.

  -  a gateway from elsewhere->SMTP SHOULD delete any return-path
     header present in the message, and either copy that information to
     the SMTP envelope or combine it with information present in the
     envelope of the other transport system to construct the reverse
     path argument to the MAIL command in the SMTP envelope.

  The server must give special treatment to cases in which the
  processing following the end of mail data indication is only
  partially successful.  This could happen if, after accepting several
  recipients and the mail data, the SMTP server finds that the mail
  data could be successfully delivered to some, but not all, of the
  recipients.  In such cases, the response to the DATA command MUST be
  an OK reply.  However, the SMTP server MUST compose and send an
  "undeliverable mail" notification message to the originator of the
  message.



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  A single notification listing all of the failed recipients or
  separate notification messages MUST be sent for each failed
  recipient.  For economy of processing by the sender, the former is
  preferred when possible.  All undeliverable mail notification
  messages are sent using the MAIL command (even if they result from
  processing the obsolete SEND, SOML, or SAML commands) and use a null
  return path as discussed in section 3.7.

  The time stamp line and the return path line are formally defined as
  follows:

Return-path-line = "Return-Path:" FWS Reverse-path <CRLF>

Time-stamp-line = "Received:" FWS Stamp <CRLF>

Stamp = From-domain By-domain Opt-info ";"  FWS date-time

     ; where "date-time" is as defined in [32]
     ; but the "obs-" forms, especially two-digit
     ; years, are prohibited in SMTP and MUST NOT be used.

From-domain = "FROM" FWS Extended-Domain CFWS

By-domain = "BY" FWS Extended-Domain CFWS

Extended-Domain = Domain /
          ( Domain FWS "(" TCP-info ")" ) /
          ( Address-literal FWS "(" TCP-info ")" )

TCP-info = Address-literal / ( Domain FWS Address-literal )
     ; Information derived by server from TCP connection
     ; not client EHLO.

Opt-info = [Via] [With] [ID] [For]

Via = "VIA" FWS Link CFWS

With = "WITH" FWS Protocol CFWS

ID = "ID" FWS String / msg-id CFWS

For = "FOR" FWS 1*( Path / Mailbox ) CFWS

Link = "TCP" / Addtl-Link
Addtl-Link = Atom
     ; Additional standard names for links are registered with the
        ; Internet Assigned Numbers Authority (IANA).  "Via" is
        ; primarily of value with non-Internet transports.  SMTP



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        ; servers SHOULD NOT use unregistered names.
Protocol = "ESMTP" / "SMTP" / Attdl-Protocol
Attdl-Protocol = Atom
     ; Additional standard names for protocols are registered with the
        ; Internet Assigned Numbers Authority (IANA).  SMTP servers
        ; SHOULD NOT use unregistered names.

4.5 Additional Implementation Issues

4.5.1 Minimum Implementation

  In order to make SMTP workable, the following minimum implementation
  is required for all receivers.  The following commands MUST be
  supported to conform to this specification:

     EHLO
     HELO
     MAIL
     RCPT
     DATA
     RSET
     NOOP
     QUIT
     VRFY

  Any system that includes an SMTP server supporting mail relaying or
  delivery MUST support the reserved mailbox "postmaster" as a case-
  insensitive local name.  This postmaster address is not strictly
  necessary if the server always returns 554 on connection opening (as
  described in section 3.1).  The requirement to accept mail for
  postmaster implies that RCPT commands which specify a mailbox for
  postmaster at any of the domains for which the SMTP server provides
  mail service, as well as the special case of "RCPT TO:<Postmaster>"
  (with no domain specification), MUST be supported.

  SMTP systems are expected to make every reasonable effort to accept
  mail directed to Postmaster from any other system on the Internet.
  In extreme cases --such as to contain a denial of service attack or
  other breach of security-- an SMTP server may block mail directed to
  Postmaster.  However, such arrangements SHOULD be narrowly tailored
  so as to avoid blocking messages which are not part of such attacks.

4.5.2 Transparency

  Without some provision for data transparency, the character sequence
  "<CRLF>.<CRLF>" ends the mail text and cannot be sent by the user.
  In general, users are not aware of such "forbidden" sequences.  To




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  allow all user composed text to be transmitted transparently, the
  following procedures are used:

  -  Before sending a line of mail text, the SMTP client checks the
     first character of the line.  If it is a period, one additional
     period is inserted at the beginning of the line.

  -  When a line of mail text is received by the SMTP server, it checks
     the line.  If the line is composed of a single period, it is
     treated as the end of mail indicator.  If the first character is a
     period and there are other characters on the line, the first
     character is deleted.

  The mail data may contain any of the 128 ASCII characters.  All
  characters are to be delivered to the recipient's mailbox, including
  spaces, vertical and horizontal tabs, and other control characters.
  If the transmission channel provides an 8-bit byte (octet) data
  stream, the 7-bit ASCII codes are transmitted right justified in the
  octets, with the high order bits cleared to zero.  See 3.7 for
  special treatment of these conditions in SMTP systems serving a relay
  function.

  In some systems it may be necessary to transform the data as it is
  received and stored.  This may be necessary for hosts that use a
  different character set than ASCII as their local character set, that
  store data in records rather than strings, or which use special
  character sequences as delimiters inside mailboxes.  If such
  transformations are necessary, they MUST be reversible, especially if
  they are applied to mail being relayed.

4.5.3 Sizes and Timeouts

4.5.3.1 Size limits and minimums

  There are several objects that have required minimum/maximum sizes.
  Every implementation MUST be able to receive objects of at least
  these sizes.  Objects larger than these sizes SHOULD be avoided when
  possible.  However, some Internet mail constructs such as encoded
  X.400 addresses [16] will often require larger objects: clients MAY
  attempt to transmit these, but MUST be prepared for a server to
  reject them if they cannot be handled by it.  To the maximum extent
  possible, implementation techniques which impose no limits on the
  length of these objects should be used.

  local-part
     The maximum total length of a user name or other local-part is 64
     characters.




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  domain
     The maximum total length of a domain name or number is 255
     characters.

  path
     The maximum total length of a reverse-path or forward-path is 256
     characters (including the punctuation and element separators).

  command line
     The maximum total length of a command line including the command
     word and the <CRLF> is 512 characters.  SMTP extensions may be
     used to increase this limit.

  reply line
     The maximum total length of a reply line including the reply code
     and the <CRLF> is 512 characters.  More information may be
     conveyed through multiple-line replies.

  text line
     The maximum total length of a text line including the <CRLF> is
     1000 characters (not counting the leading dot duplicated for
     transparency).  This number may be increased by the use of SMTP
     Service Extensions.

  message content
     The maximum total length of a message content (including any
     message headers as well as the message body) MUST BE at least 64K
     octets.  Since the introduction of Internet standards for
     multimedia mail [12], message lengths on the Internet have grown
     dramatically, and message size restrictions should be avoided if
     at all possible.  SMTP server systems that must impose
     restrictions SHOULD implement the "SIZE" service extension [18],
     and SMTP client systems that will send large messages SHOULD
     utilize it when possible.

  recipients buffer
     The minimum total number of recipients that must be buffered is
     100 recipients.  Rejection of messages (for excessive recipients)
     with fewer than 100 RCPT commands is a violation of this
     specification.  The general principle that relaying SMTP servers
     MUST NOT, and delivery SMTP servers SHOULD NOT, perform validation
     tests on message headers suggests that rejecting a message based
     on the total number of recipients shown in header fields is to be
     discouraged.  A server which imposes a limit on the number of
     recipients MUST behave in an orderly fashion,  such as to reject
     additional addresses over its limit rather than silently
     discarding addresses previously accepted.  A client that needs to




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RFC 2821             Simple Mail Transfer Protocol            April 2001


     deliver a message containing over 100 RCPT commands SHOULD be
     prepared to transmit in 100-recipient "chunks" if the server
     declines to accept more than 100 recipients in a single message.

  Errors due to exceeding these limits may be reported by using the
  reply codes.  Some examples of reply codes are:

     500 Line too long.
  or
     501 Path too long
  or
     452 Too many recipients  (see below)
  or
     552 Too much mail data.

  RFC 821 [30] incorrectly listed the error where an SMTP server
  exhausts its implementation limit on the number of RCPT commands
  ("too many recipients") as having reply code 552.  The correct reply
  code for this condition is 452.  Clients SHOULD treat a 552 code in
  this case as a temporary, rather than permanent, failure so the logic
  below works.

  When a conforming SMTP server encounters this condition, it has at
  least 100 successful RCPT commands in its recipients buffer.  If the
  server is able to accept the message, then at least these 100
  addresses will be removed from the SMTP client's queue.  When the
  client attempts retransmission of those addresses which received 452
  responses, at least 100 of these will be able to fit in the SMTP
  server's recipients buffer.  Each retransmission attempt which is
  able to deliver anything will be able to dispose of at least 100 of
  these recipients.

  If an SMTP server has an implementation limit on the number of RCPT
  commands and this limit is exhausted, it MUST use a response code of
  452 (but the client SHOULD also be prepared for a 552, as noted
  above).  If the server has a configured site-policy limitation on the
  number of RCPT commands, it MAY instead use a 5XX response code.
  This would be most appropriate if the policy limitation was intended
  to apply if the total recipient count for a particular message body
  were enforced even if that message body was sent in multiple mail
  transactions.

4.5.3.2 Timeouts

  An SMTP client MUST provide a timeout mechanism.  It MUST use per-
  command timeouts rather than somehow trying to time the entire mail
  transaction.  Timeouts SHOULD be easily reconfigurable, preferably
  without recompiling the SMTP code.  To implement this, a timer is set



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  for each SMTP command and for each buffer of the data transfer.  The
  latter means that the overall timeout is inherently proportional to
  the size of the message.

  Based on extensive experience with busy mail-relay hosts, the minimum
  per-command timeout values SHOULD be as follows:

  Initial 220 Message: 5 minutes
     An SMTP client process needs to distinguish between a failed TCP
     connection and a delay in receiving the initial 220 greeting
     message.  Many SMTP servers accept a TCP connection but delay
     delivery of the 220 message until their system load permits more
     mail to be processed.

  MAIL Command: 5 minutes

  RCPT Command: 5 minutes
     A longer timeout is required if processing of mailing lists and
     aliases is not deferred until after the message was accepted.

  DATA Initiation: 2 minutes
     This is while awaiting the "354 Start Input" reply to a DATA
     command.

  Data Block: 3 minutes
     This is while awaiting the completion of each TCP SEND call
     transmitting a chunk of data.

  DATA Termination: 10 minutes.
     This is while awaiting the "250 OK" reply.  When the receiver gets
     the final period terminating the message data, it typically
     performs processing to deliver the message to a user mailbox.  A
     spurious timeout at this point would be very wasteful and would
     typically result in delivery of multiple copies of the message,
     since it has been successfully sent and the server has accepted
     responsibility for delivery.  See section 6.1 for additional
     discussion.

  An SMTP server SHOULD have a timeout of at least 5 minutes while it
  is awaiting the next command from the sender.

4.5.4 Retry Strategies

  The common structure of a host SMTP implementation includes user
  mailboxes, one or more areas for queuing messages in transit, and one
  or more daemon processes for sending and receiving mail.  The exact
  structure will vary depending on the needs of the users on the host




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  and the number and size of mailing lists supported by the host.  We
  describe several optimizations that have proved helpful, particularly
  for mailers supporting high traffic levels.

  Any queuing strategy MUST include timeouts on all activities on a
  per-command basis.  A queuing strategy MUST NOT send error messages
  in response to error messages under any circumstances.

4.5.4.1 Sending Strategy

  The general model for an SMTP client is one or more processes that
  periodically attempt to transmit outgoing mail.  In a typical system,
  the program that composes a message has some method for requesting
  immediate attention for a new piece of outgoing mail, while mail that
  cannot be transmitted immediately MUST be queued and periodically
  retried by the sender.  A mail queue entry will include not only the
  message itself but also the envelope information.

  The sender MUST delay retrying a particular destination after one
  attempt has failed.  In general, the retry interval SHOULD be at
  least 30 minutes; however, more sophisticated and variable strategies
  will be beneficial when the SMTP client can determine the reason for
  non-delivery.

  Retries continue until the message is transmitted or the sender gives
  up; the give-up time generally needs to be at least 4-5 days.  The
  parameters to the retry algorithm MUST be configurable.

  A client SHOULD keep a list of hosts it cannot reach and
  corresponding connection timeouts, rather than just retrying queued
  mail items.

  Experience suggests that failures are typically transient (the target
  system or its connection has crashed), favoring a policy of two
  connection attempts in the first hour the message is in the queue,
  and then backing off to one every two or three hours.

  The SMTP client can shorten the queuing delay in cooperation with the
  SMTP server.  For example, if mail is received from a particular
  address, it is likely that mail queued for that host can now be sent.
  Application of this principle may, in many cases, eliminate the
  requirement for an explicit "send queues now" function such as ETRN
  [9].

  The strategy may be further modified as a result of multiple
  addresses per host (see below) to optimize delivery time vs. resource
  usage.




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  An SMTP client may have a large queue of messages for each
  unavailable destination host.  If all of these messages were retried
  in every retry cycle, there would be excessive Internet overhead and
  the sending system would be blocked for a long period.  Note that an
  SMTP client can generally determine that a delivery attempt has
  failed only after a timeout of several minutes and even a one-minute
  timeout per connection will result in a very large delay if retries
  are repeated for dozens, or even hundreds, of queued messages to the
  same host.

  At the same time, SMTP clients SHOULD use great care in caching
  negative responses from servers.  In an extreme case, if EHLO is
  issued multiple times during the same SMTP connection, different
  answers may be returned by the server.  More significantly, 5yz
  responses to the MAIL command MUST NOT be cached.

  When a mail message is to be delivered to multiple recipients, and
  the SMTP server to which a copy of the message is to be sent is the
  same for multiple recipients, then only one copy of the message
  SHOULD be transmitted.  That is, the SMTP client SHOULD use the
  command sequence:  MAIL, RCPT, RCPT,... RCPT, DATA instead of the
  sequence: MAIL, RCPT, DATA, ..., MAIL, RCPT, DATA.  However, if there
  are very many addresses, a limit on the number of RCPT commands per
  MAIL command MAY be imposed.  Implementation of this efficiency
  feature is strongly encouraged.

  Similarly, to achieve timely delivery, the SMTP client MAY support
  multiple concurrent outgoing mail transactions.  However, some limit
  may be appropriate to protect the host from devoting all its
  resources to mail.

4.5.4.2 Receiving Strategy

  The SMTP server SHOULD attempt to keep a pending listen on the SMTP
  port at all times.  This requires the support of multiple incoming
  TCP connections for SMTP.  Some limit MAY be imposed but servers that
  cannot handle more than one SMTP transaction at a time are not in
  conformance with the intent of this specification.

  As discussed above, when the SMTP server receives mail from a
  particular host address, it could activate its own SMTP queuing
  mechanisms to retry any mail pending for that host address.

4.5.5   Messages with a null reverse-path

  There are several types of notification messages which are required
  by existing and proposed standards to be sent with a null reverse
  path, namely non-delivery notifications as discussed in section 3.7,



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  other kinds of Delivery Status Notifications (DSNs) [24], and also
  Message Disposition Notifications (MDNs) [10].  All of these kinds of
  messages are notifications about a previous message, and they are
  sent to the reverse-path of the previous mail message.  (If the
  delivery of such a notification message fails, that usually indicates
  a problem with the mail system of the host to which the notification
  message is addressed.  For this reason, at some hosts the MTA is set
  up to forward such failed notification messages to someone who is
  able to fix problems with the mail system, e.g., via the postmaster
  alias.)

  All other types of messages (i.e., any message which is not required
  by a standards-track RFC to have a null reverse-path) SHOULD be sent
  with with a valid, non-null reverse-path.

  Implementors of automated email processors should be careful to make
  sure that the various kinds of messages with null reverse-path are
  handled correctly, in particular such systems SHOULD NOT reply to
  messages with null reverse-path.

5. Address Resolution and Mail Handling

  Once an SMTP client lexically identifies a domain to which mail will
  be delivered for processing (as described in sections 3.6 and 3.7), a
  DNS lookup MUST be performed to resolve the domain name [22].  The
  names are expected to be fully-qualified domain names (FQDNs):
  mechanisms for inferring FQDNs from partial names or local aliases
  are outside of this specification and, due to a history of problems,
  are generally discouraged.  The lookup first attempts to locate an MX
  record associated with the name.  If a CNAME record is found instead,
  the resulting name is processed as if it were the initial name.  If
  no MX records are found, but an A RR is found, the A RR is treated as
  if it was associated with an implicit MX RR, with a preference of 0,
  pointing to that host.  If one or more MX RRs are found for a given
  name, SMTP systems MUST NOT utilize any A RRs associated with that
  name unless they are located using the MX RRs; the "implicit MX" rule
  above applies only if there are no MX records present.  If MX records
  are present, but none of them are usable, this situation MUST be
  reported as an error.

  When the lookup succeeds, the mapping can result in a list of
  alternative delivery addresses rather than a single address, because
  of multiple MX records, multihoming, or both.  To provide reliable
  mail transmission, the SMTP client MUST be able to try (and retry)
  each of the relevant addresses in this list in order, until a
  delivery attempt succeeds.  However, there MAY also be a configurable
  limit on the number of alternate addresses that can be tried.  In any
  case, the SMTP client SHOULD try at least two addresses.



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  Two types of information is used to rank the host addresses: multiple
  MX records, and multihomed hosts.

  Multiple MX records contain a preference indication that MUST be used
  in sorting (see below).  Lower numbers are more preferred than higher
  ones.  If there are multiple destinations with the same preference
  and there is no clear reason to favor one (e.g., by recognition of an
  easily-reached address), then the sender-SMTP MUST randomize them to
  spread the load across multiple mail exchangers for a specific
  organization.

  The destination host (perhaps taken from the preferred MX record) may
  be multihomed, in which case the domain name resolver will return a
  list of alternative IP addresses.  It is the responsibility of the
  domain name resolver interface to have ordered this list by
  decreasing preference if necessary, and SMTP MUST try them in the
  order presented.

  Although the capability to try multiple alternative addresses is
  required, specific installations may want to limit or disable the use
  of alternative addresses.  The question of whether a sender should
  attempt retries using the different addresses of a multihomed host
  has been controversial.  The main argument for using the multiple
  addresses is that it maximizes the probability of timely delivery,
  and indeed sometimes the probability of any delivery; the counter-
  argument is that it may result in unnecessary resource use.  Note
  that resource use is also strongly determined by the sending strategy
  discussed in section 4.5.4.1.

  If an SMTP server receives a message with a destination for which it
  is a designated Mail eXchanger, it MAY relay the message (potentially
  after having rewritten the MAIL FROM and/or RCPT TO addresses), make
  final delivery of the message, or hand it off using some mechanism
  outside the SMTP-provided transport environment.  Of course, neither
  of the latter require that the list of MX records be examined
  further.

  If it determines that it should relay the message without rewriting
  the address, it MUST sort the MX records to determine candidates for
  delivery.  The records are first ordered by preference, with the
  lowest-numbered records being most preferred.  The relay host MUST
  then inspect the list for any of the names or addresses by which it
  might be known in mail transactions.  If a matching record is found,
  all records at that preference level and higher-numbered ones MUST be
  discarded from consideration.  If there are no records left at that
  point, it is an error condition, and the message MUST be returned as
  undeliverable.  If records do remain, they SHOULD be tried, best
  preference first, as described above.



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6. Problem Detection and Handling

6.1 Reliable Delivery and Replies by Email

  When the receiver-SMTP accepts a piece of mail (by sending a "250 OK"
  message in response to DATA), it is accepting responsibility for
  delivering or relaying the message.  It must take this responsibility
  seriously.  It MUST NOT lose the message for frivolous reasons, such
  as because the host later crashes or because of a predictable
  resource shortage.

  If there is a delivery failure after acceptance of a message, the
  receiver-SMTP MUST formulate and mail a notification message.  This
  notification MUST be sent using a null ("<>") reverse path in the
  envelope.  The recipient of this notification MUST be the address
  from the envelope return path (or the Return-Path: line).  However,
  if this address is null ("<>"), the receiver-SMTP MUST NOT send a
  notification.  Obviously, nothing in this section can or should
  prohibit local decisions (i.e., as part of the same system
  environment as the receiver-SMTP) to log or otherwise transmit
  information about null address events locally if that is desired.  If
  the address is an explicit source route, it MUST be stripped down to
  its final hop.

  For example, suppose that an error notification must be sent for a
  message that arrived with:

     MAIL FROM:<@a,@b:user@d>

  The notification message MUST be sent using:

     RCPT TO:<user@d>

  Some delivery failures after the message is accepted by SMTP will be
  unavoidable.  For example, it may be impossible for the receiving
  SMTP server to validate all the delivery addresses in RCPT command(s)
  due to a "soft" domain system error, because the target is a mailing
  list (see earlier discussion of RCPT), or because the server is
  acting as a relay and has no immediate access to the delivering
  system.

  To avoid receiving duplicate messages as the result of timeouts, a
  receiver-SMTP MUST seek to minimize the time required to respond to
  the final <CRLF>.<CRLF> end of data indicator.  See RFC 1047 [28] for
  a discussion of this problem.






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6.2 Loop Detection

  Simple counting of the number of "Received:" headers in a message has
  proven to be an effective, although rarely optimal, method of
  detecting loops in mail systems.  SMTP servers using this technique
  SHOULD use a large rejection threshold, normally at least 100
  Received entries.  Whatever mechanisms are used, servers MUST contain
  provisions for detecting and stopping trivial loops.

6.3 Compensating for Irregularities

  Unfortunately, variations, creative interpretations, and outright
  violations of Internet mail protocols do occur; some would suggest
  that they occur quite frequently.  The debate as to whether a well-
  behaved SMTP receiver or relay should reject a malformed message,
  attempt to pass it on unchanged, or attempt to repair it to increase
  the odds of successful delivery (or subsequent reply) began almost
  with the dawn of structured network mail and shows no signs of
  abating.  Advocates of rejection claim that attempted repairs are
  rarely completely adequate and that rejection of bad messages is the
  only way to get the offending software repaired.  Advocates of
  "repair" or "deliver no matter what" argue that users prefer that
  mail go through it if at all possible and that there are significant
  market pressures in that direction.  In practice, these market
  pressures may be more important to particular vendors than strict
  conformance to the standards, regardless of the preference of the
  actual developers.

  The problems associated with ill-formed messages were exacerbated by
  the introduction of the split-UA mail reading protocols [3, 26, 5,
  21].  These protocols have encouraged the use of SMTP as a posting
  protocol, and SMTP servers as relay systems for these client hosts
  (which are often only intermittently connected to the Internet).
  Historically, many of those client machines lacked some of the
  mechanisms and information assumed by SMTP (and indeed, by the mail
  format protocol [7]).  Some could not keep adequate track of time;
  others had no concept of time zones; still others could not identify
  their own names or addresses; and, of course, none could satisfy the
  assumptions that underlay RFC 822's conception of authenticated
  addresses.

  In response to these weak SMTP clients, many SMTP systems now
  complete messages that are delivered to them in incomplete or
  incorrect form.  This strategy is generally considered appropriate
  when the server can identify or authenticate the client, and there
  are prior agreements between them.  By contrast, there is at best
  great concern about fixes applied by a relay or delivery SMTP server
  that has little or no knowledge of the user or client machine.



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  The following changes to a message being processed MAY be applied
  when necessary by an originating SMTP server, or one used as the
  target of SMTP as an initial posting protocol:

  -  Addition of a message-id field when none appears

  -  Addition of a date, time or time zone when none appears

  -  Correction of addresses to proper FQDN format

  The less information the server has about the client, the less likely
  these changes are to be correct and the more caution and conservatism
  should be applied when considering whether or not to perform fixes
  and how.  These changes MUST NOT be applied by an SMTP server that
  provides an intermediate relay function.

  In all cases, properly-operating clients supplying correct
  information are preferred to corrections by the SMTP server.  In all
  cases, documentation of actions performed by the servers (in trace
  fields and/or header comments) is strongly encouraged.

7. Security Considerations

7.1 Mail Security and Spoofing

  SMTP mail is inherently insecure in that it is feasible for even
  fairly casual users to negotiate directly with receiving and relaying
  SMTP servers and create messages that will trick a naive recipient
  into believing that they came from somewhere else.  Constructing such
  a message so that the "spoofed" behavior cannot be detected by an
  expert is somewhat more difficult, but not sufficiently so as to be a
  deterrent to someone who is determined and knowledgeable.
  Consequently, as knowledge of Internet mail increases, so does the
  knowledge that SMTP mail inherently cannot be authenticated, or
  integrity checks provided, at the transport level.  Real mail
  security lies only in end-to-end methods involving the message
  bodies, such as those which use digital signatures (see [14] and,
  e.g., PGP [4] or S/MIME [31]).

  Various protocol extensions and configuration options that provide
  authentication at the transport level (e.g., from an SMTP client to
  an SMTP server) improve somewhat on the traditional situation
  described above.  However, unless they are accompanied by careful
  handoffs of responsibility in a carefully-designed trust environment,
  they remain inherently weaker than end-to-end mechanisms which use
  digitally signed messages rather than depending on the integrity of
  the transport system.




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  Efforts to make it more difficult for users to set envelope return
  path and header "From" fields to point to valid addresses other than
  their own are largely misguided: they frustrate legitimate
  applications in which mail is sent by one user on behalf of another
  or in which error (or normal) replies should be directed to a special
  address.  (Systems that provide convenient ways for users to alter
  these fields on a per-message basis should attempt to establish a
  primary and permanent mailbox address for the user so that Sender
  fields within the message data can be generated sensibly.)

  This specification does not further address the authentication issues
  associated with SMTP other than to advocate that useful functionality
  not be disabled in the hope of providing some small margin of
  protection against an ignorant user who is trying to fake mail.

7.2 "Blind" Copies

  Addresses that do not appear in the message headers may appear in the
  RCPT commands to an SMTP server for a number of reasons.  The two
  most common involve the use of a mailing address as a "list exploder"
  (a single address that resolves into multiple addresses) and the
  appearance of "blind copies".  Especially when more than one RCPT
  command is present, and in order to avoid defeating some of the
  purpose of these mechanisms, SMTP clients and servers SHOULD NOT copy
  the full set of RCPT command arguments into the headers, either as
  part of trace headers or as informational or private-extension
  headers.  Since this rule is often violated in practice, and cannot
  be enforced, sending SMTP systems that are aware of "bcc" use MAY
  find it helpful to send each blind copy as a separate message
  transaction containing only a single RCPT command.

  There is no inherent relationship between either "reverse" (from
  MAIL, SAML, etc., commands) or "forward" (RCPT) addresses in the SMTP
  transaction ("envelope") and the addresses in the headers.  Receiving
  systems SHOULD NOT attempt to deduce such relationships and use them
  to alter the headers of the message for delivery.  The popular
  "Apparently-to" header is a violation of this principle as well as a
  common source of unintended information disclosure and SHOULD NOT be
  used.

7.3 VRFY, EXPN, and Security

  As discussed in section 3.5, individual sites may want to disable
  either or both of VRFY or EXPN for security reasons.  As a corollary
  to the above, implementations that permit this MUST NOT appear to
  have verified addresses that are not, in fact, verified.  If a site





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  disables these commands for security reasons, the SMTP server MUST
  return a 252 response, rather than a code that could be confused with
  successful or unsuccessful verification.

  Returning a 250 reply code with the address listed in the VRFY
  command after having checked it only for syntax violates this rule.
  Of course, an implementation that "supports" VRFY by always returning
  550 whether or not the address is valid is equally not in
  conformance.

  Within the last few years, the contents of mailing lists have become
  popular as an address information source for so-called "spammers."
  The use of EXPN to "harvest" addresses has increased as list
  administrators have installed protections against inappropriate uses
  of the lists themselves.  Implementations SHOULD still provide
  support for EXPN, but sites SHOULD carefully evaluate the tradeoffs.
  As authentication mechanisms are introduced into SMTP, some sites may
  choose to make EXPN available only to authenticated requestors.

7.4 Information Disclosure in Announcements

  There has been an ongoing debate about the tradeoffs between the
  debugging advantages of announcing server type and version (and,
  sometimes, even server domain name) in the greeting response or in
  response to the HELP command and the disadvantages of exposing
  information that might be useful in a potential hostile attack.  The
  utility of the debugging information is beyond doubt.  Those who
  argue for making it available point out that it is far better to
  actually secure an SMTP server rather than hope that trying to
  conceal known vulnerabilities by hiding the server's precise identity
  will provide more protection.  Sites are encouraged to evaluate the
  tradeoff with that issue in mind; implementations are strongly
  encouraged to minimally provide for making type and version
  information available in some way to other network hosts.

7.5 Information Disclosure in Trace Fields

  In some circumstances, such as when mail originates from within a LAN
  whose hosts are not directly on the public Internet, trace
  ("Received") fields produced in conformance with this specification
  may disclose host names and similar information that would not
  normally be available.  This ordinarily does not pose a problem, but
  sites with special concerns about name disclosure should be aware of
  it.  Also, the optional FOR clause should be supplied with caution or
  not at all when multiple recipients are involved lest it
  inadvertently disclose the identities of "blind copy" recipients to
  others.




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7.6 Information Disclosure in Message Forwarding

  As discussed in section 3.4, use of the 251 or 551 reply codes to
  identify the replacement address associated with a mailbox may
  inadvertently disclose sensitive information.  Sites that are
  concerned about those issues should ensure that they select and
  configure servers appropriately.

7.7 Scope of Operation of SMTP Servers

  It is a well-established principle that an SMTP server may refuse to
  accept mail for any operational or technical reason that makes sense
  to the site providing the server.  However, cooperation among sites
  and installations makes the Internet possible.  If sites take
  excessive advantage of the right to reject traffic, the ubiquity of
  email availability (one of the strengths of the Internet) will be
  threatened; considerable care should be taken and balance maintained
  if a site decides to be selective about the traffic it will accept
  and process.

  In recent years, use of the relay function through arbitrary sites
  has been used as part of hostile efforts to hide the actual origins
  of mail.  Some sites have decided to limit the use of the relay
  function to known or identifiable sources, and implementations SHOULD
  provide the capability to perform this type of filtering.  When mail
  is rejected for these or other policy reasons, a 550 code SHOULD be
  used in response to EHLO, MAIL, or RCPT as appropriate.

8. IANA Considerations

  IANA will maintain three registries in support of this specification.
  The first consists of SMTP service extensions with the associated
  keywords, and, as needed, parameters and verbs.  As specified in
  section 2.2.2, no entry may be made in this registry that starts in
  an "X".  Entries may be made only for service extensions (and
  associated keywords, parameters, or verbs) that are defined in
  standards-track or experimental RFCs specifically approved by the
  IESG for this purpose.

  The second registry consists of "tags" that identify forms of domain
  literals other than those for IPv4 addresses (specified in RFC 821
  and in this document) and IPv6 addresses (specified in this
  document).  Additional literal types require standardization before
  being used; none are anticipated at this time.

  The third, established by RFC 821 and renewed by this specification,
  is a registry of link and protocol identifiers to be used with the
  "via" and "with" subclauses of the time stamp ("Received: header")



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  described in section 4.4.  Link and protocol identifiers in addition
  to those specified in this document may be registered only by
  standardization or by way of an RFC-documented, IESG-approved,
  Experimental protocol extension.

9. References

  [1]  American National Standards Institute (formerly United States of
       America Standards Institute), X3.4, 1968, "USA Code for
       Information Interchange". ANSI X3.4-1968 has been replaced by
       newer versions with slight modifications, but the 1968 version
       remains definitive for the Internet.

  [2]  Braden, R., "Requirements for Internet hosts - application and
       support", STD 3, RFC 1123, October 1989.

  [3]  Butler, M., Chase, D., Goldberger, J., Postel, J. and J.
       Reynolds, "Post Office Protocol - version 2", RFC 937, February
       1985.

  [4]  Callas, J., Donnerhacke, L., Finney, H. and R. Thayer, "OpenPGP
       Message Format", RFC 2440, November 1998.

  [5]  Crispin, M., "Interactive Mail Access Protocol - Version 2", RFC
       1176, August 1990.

  [6]  Crispin, M., "Internet Message Access Protocol - Version 4", RFC
       2060, December 1996.

  [7]  Crocker, D., "Standard for the Format of ARPA Internet Text
       Messages", RFC 822, August 1982.

  [8]  Crocker, D. and P. Overell, Eds., "Augmented BNF for Syntax
       Specifications: ABNF", RFC 2234, November 1997.

  [9]  De Winter, J., "SMTP Service Extension for Remote Message Queue
       Starting", RFC 1985, August 1996.

  [10] Fajman, R., "An Extensible Message Format for Message
       Disposition Notifications", RFC 2298, March 1998.

  [11] Freed, N, "Behavior of and Requirements for Internet Firewalls",
       RFC 2979, October 2000.

  [12] Freed, N. and N. Borenstein, "Multipurpose Internet Mail
       Extensions (MIME) Part One: Format of Internet Message Bodies",
       RFC 2045, December 1996.




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  [13] Freed, N., "SMTP Service Extension for Command Pipelining", RFC
       2920, September 2000.

  [14] Galvin, J., Murphy, S., Crocker, S. and N. Freed, "Security
       Multiparts for MIME: Multipart/Signed and Multipart/Encrypted",
       RFC 1847, October 1995.

  [15] Gellens, R. and J. Klensin, "Message Submission", RFC 2476,
       December 1998.

  [16] Kille, S., "Mapping between X.400 and RFC822/MIME", RFC 2156,
       January 1998.

  [17] Hinden, R and S. Deering, Eds. "IP Version 6 Addressing
       Architecture", RFC 2373, July 1998.

  [18] Klensin, J., Freed, N. and K. Moore, "SMTP Service Extension for
       Message Size Declaration", STD 10, RFC 1870, November 1995.

  [19] Klensin, J., Freed, N., Rose, M., Stefferud, E. and D. Crocker,
       "SMTP Service Extensions", STD 10, RFC 1869, November 1995.

  [20] Klensin, J., Freed, N., Rose, M., Stefferud, E. and D. Crocker,
       "SMTP Service Extension for 8bit-MIMEtransport", RFC 1652, July
       1994.

  [21] Lambert, M., "PCMAIL: A distributed mail system for personal
       computers", RFC 1056, July 1988.

  [22] Mockapetris, P., "Domain names - implementation and
       specification", STD 13, RFC 1035, November 1987.

       Mockapetris, P., "Domain names - concepts and facilities", STD
       13, RFC 1034, November 1987.

  [23] Moore, K., "MIME (Multipurpose Internet Mail Extensions) Part
       Three: Message Header Extensions for Non-ASCII Text", RFC 2047,
       December 1996.

  [24] Moore, K., "SMTP Service Extension for Delivery Status
       Notifications", RFC 1891, January 1996.

  [25] Moore, K., and G. Vaudreuil, "An Extensible Message Format for
       Delivery Status Notifications", RFC 1894, January 1996.

  [26] Myers, J. and M. Rose, "Post Office Protocol - Version 3", STD
       53, RFC 1939, May 1996.




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  [27] Partridge, C., "Mail routing and the domain system", RFC 974,
       January 1986.

  [28] Partridge, C., "Duplicate messages and SMTP", RFC 1047, February
       1988.

  [29] Postel, J., ed., "Transmission Control Protocol - DARPA Internet
       Program Protocol Specification", STD 7, RFC 793, September 1981.

  [30] Postel, J., "Simple Mail Transfer Protocol", RFC 821, August
       1982.

  [31] Ramsdell, B., Ed., "S/MIME Version 3 Message Specification", RFC
       2633, June 1999.

  [32] Resnick, P., Ed., "Internet Message Format", RFC 2822, April
       2001.

  [33] Vaudreuil, G., "SMTP Service Extensions for Transmission of
       Large and Binary MIME Messages", RFC 1830, August 1995.

  [34] Vaudreuil, G., "Enhanced Mail System Status Codes", RFC 1893,
       January 1996.

10. Editor's Address

  John C. Klensin
  AT&T Laboratories
  99 Bedford St
  Boston, MA 02111 USA

  Phone: 617-574-3076
  EMail: [email protected]

11. Acknowledgments

  Many people worked long and hard on the many iterations of this
  document.  There was wide-ranging debate in the IETF DRUMS Working
  Group, both on its mailing list and in face to face discussions,
  about many technical issues and the role of a revised standard for
  Internet mail transport, and many contributors helped form the
  wording in this specification.  The hundreds of participants in the
  many discussions since RFC 821 was produced are too numerous to
  mention, but they all helped this document become what it is.







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RFC 2821             Simple Mail Transfer Protocol            April 2001


APPENDICES

A. TCP Transport Service

  The TCP connection supports the transmission of 8-bit bytes.  The
  SMTP data is 7-bit ASCII characters.  Each character is transmitted
  as an 8-bit byte with the high-order bit cleared to zero.  Service
  extensions may modify this rule to permit transmission of full 8-bit
  data bytes as part of the message body, but not in SMTP commands or
  responses.

B. Generating SMTP Commands from RFC 822 Headers

  Some systems use RFC 822 headers (only) in a mail submission
  protocol, or otherwise generate SMTP commands from RFC 822 headers
  when such a message is handed to an MTA from a UA.  While the MTA-UA
  protocol is a private matter, not covered by any Internet Standard,
  there are problems with this approach.  For example, there have been
  repeated problems with proper handling of "bcc" copies and
  redistribution lists when information that conceptually belongs to a
  mail envelopes is not separated early in processing from header
  information (and kept separate).

  It is recommended that the UA provide its initial ("submission
  client") MTA with an envelope separate from the message itself.
  However, if the envelope is not supplied, SMTP commands SHOULD be
  generated as follows:

  1. Each recipient address from a TO, CC, or BCC header field SHOULD
     be copied to a RCPT command (generating multiple message copies if
     that is required for queuing or delivery).  This includes any
     addresses listed in a RFC 822 "group".  Any BCC fields SHOULD then
     be removed from the headers.  Once this process is completed, the
     remaining headers SHOULD be checked to verify that at least one
     To:, Cc:, or Bcc: header remains.  If none do, then a bcc: header
     with no additional information SHOULD be inserted as specified in
     [32].

  2. The return address in the MAIL command SHOULD, if possible, be
     derived from the system's identity for the submitting (local)
     user, and the "From:" header field otherwise.  If there is a
     system identity available, it SHOULD also be copied to the Sender
     header field if it is different from the address in the From
     header field.  (Any Sender field that was already there SHOULD be
     removed.)  Systems may provide a way for submitters to override
     the envelope return address, but may want to restrict its use to
     privileged users.  This will not prevent mail forgery, but may
     lessen its incidence; see section 7.1.



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  When an MTA is being used in this way, it bears responsibility for
  ensuring that the message being transmitted is valid.  The mechanisms
  for checking that validity, and for handling (or returning) messages
  that are not valid at the time of arrival, are part of the MUA-MTA
  interface and not covered by this specification.

  A submission protocol based on Standard RFC 822 information alone
  MUST NOT be used to gateway a message from a foreign (non-SMTP) mail
  system into an SMTP environment.  Additional information to construct
  an envelope must come from some source in the other environment,
  whether supplemental headers or the foreign system's envelope.

  Attempts to gateway messages using only their header "to" and "cc"
  fields have repeatedly caused mail loops and other behavior adverse
  to the proper functioning of the Internet mail environment.  These
  problems have been especially common when the message originates from
  an Internet mailing list and is distributed into the foreign
  environment using envelope information.  When these messages are then
  processed by a header-only remailer, loops back to the Internet
  environment (and the mailing list) are almost inevitable.

C. Source Routes

  Historically, the <reverse-path> was a reverse source routing list of
  hosts and a source mailbox.  The first host in the <reverse-path>
  SHOULD be the host sending the MAIL command.  Similarly, the
  <forward-path> may be a source routing lists of hosts and a
  destination mailbox.  However, in general, the <forward-path> SHOULD
  contain only a mailbox and domain name, relying on the domain name
  system to supply routing information if required.  The use of source
  routes is deprecated; while servers MUST be prepared to receive and
  handle them as discussed in section 3.3 and F.2, clients SHOULD NOT
  transmit them and this section was included only to provide context.

  For relay purposes, the forward-path may be a source route of the
  form "@ONE,@TWO:JOE@THREE", where ONE, TWO, and THREE MUST BE fully-
  qualified domain names.  This form is used to emphasize the
  distinction between an address and a route.  The mailbox is an
  absolute address, and the route is information about how to get
  there.  The two concepts should not be confused.

  If source routes are used, RFC 821 and the text below should be
  consulted for the mechanisms for constructing and updating the
  forward- and reverse-paths.







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RFC 2821             Simple Mail Transfer Protocol            April 2001


  The SMTP server transforms the command arguments by moving its own
  identifier (its domain name or that of any domain for which it is
  acting as a mail exchanger), if it appears, from the forward-path to
  the beginning of the reverse-path.

  Notice that the forward-path and reverse-path appear in the SMTP
  commands and replies, but not necessarily in the message.  That is,
  there is no need for these paths and especially this syntax to appear
  in the "To:" , "From:", "CC:", etc. fields of the message header.
  Conversely, SMTP servers MUST NOT derive final message delivery
  information from message header fields.

  When the list of hosts is present, it is a "reverse" source route and
  indicates that the mail was relayed through each host on the list
  (the first host in the list was the most recent relay).  This list is
  used as a source route to return non-delivery notices to the sender.
  As each relay host adds itself to the beginning of the list, it MUST
  use its name as known in the transport environment to which it is
  relaying the mail rather than that of the transport environment from
  which the mail came (if they are different).

D. Scenarios

  This section presents complete scenarios of several types of SMTP
  sessions.  In the examples, "C:" indicates what is said by the SMTP
  client, and "S:" indicates what is said by the SMTP server.

D.1 A Typical SMTP Transaction Scenario

  This SMTP example shows mail sent by Smith at host bar.com, to Jones,
  Green, and Brown at host foo.com.  Here we assume that host bar.com
  contacts host foo.com directly.  The mail is accepted for Jones and
  Brown.  Green does not have a mailbox at host foo.com.

     S: 220 foo.com Simple Mail Transfer Service Ready
     C: EHLO bar.com
     S: 250-foo.com greets bar.com
     S: 250-8BITMIME
     S: 250-SIZE
     S: 250-DSN
     S: 250 HELP
     C: MAIL FROM:<[email protected]>
     S: 250 OK
     C: RCPT TO:<[email protected]>
     S: 250 OK
     C: RCPT TO:<[email protected]>
     S: 550 No such user here
     C: RCPT TO:<[email protected]>



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RFC 2821             Simple Mail Transfer Protocol            April 2001


     S: 250 OK
     C: DATA
     S: 354 Start mail input; end with <CRLF>.<CRLF>
     C: Blah blah blah...
     C: ...etc. etc. etc.
     C: .
     S: 250 OK
     C: QUIT
     S: 221 foo.com Service closing transmission channel

D.2 Aborted SMTP Transaction Scenario

     S: 220 foo.com Simple Mail Transfer Service Ready
     C: EHLO bar.com
     S: 250-foo.com greets bar.com
     S: 250-8BITMIME
     S: 250-SIZE
     S: 250-DSN
     S: 250 HELP
     C: MAIL FROM:<[email protected]>
     S: 250 OK
     C: RCPT TO:<[email protected]>
     S: 250 OK
     C: RCPT TO:<[email protected]>
     S: 550 No such user here
     C: RSET
     S: 250 OK
     C: QUIT
     S: 221 foo.com Service closing transmission channel

D.3 Relayed Mail Scenario

  Step 1  --  Source Host to Relay Host

     S: 220 foo.com Simple Mail Transfer Service Ready
     C: EHLO bar.com
     S: 250-foo.com greets bar.com
     S: 250-8BITMIME
     S: 250-SIZE
     S: 250-DSN
     S: 250 HELP
     C: MAIL FROM:<[email protected]>
     S: 250 OK
     C: RCPT TO:<@foo.com:[email protected]>
     S: 250 OK
     C: DATA
     S: 354 Start mail input; end with <CRLF>.<CRLF>
     C: Date: Thu, 21 May 1998 05:33:29 -0700



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RFC 2821             Simple Mail Transfer Protocol            April 2001


     C: From: John Q. Public <[email protected]>
     C: Subject:  The Next Meeting of the Board
     C: To: [email protected]
     C:
     C: Bill:
     C: The next meeting of the board of directors will be
     C: on Tuesday.
     C:                         John.
     C: .
     S: 250 OK
     C: QUIT
     S: 221 foo.com Service closing transmission channel

  Step 2  --  Relay Host to Destination Host

     S: 220 xyz.com Simple Mail Transfer Service Ready
     C: EHLO foo.com
     S: 250 xyz.com is on the air
     C: MAIL FROM:<@foo.com:[email protected]>
     S: 250 OK
     C: RCPT TO:<[email protected]>
     S: 250 OK
     C: DATA
     S: 354 Start mail input; end with <CRLF>.<CRLF>
     C: Received: from bar.com by foo.com ; Thu, 21 May 1998
     C:     05:33:29 -0700
     C: Date: Thu, 21 May 1998 05:33:22 -0700
     C: From: John Q. Public <[email protected]>
     C: Subject:  The Next Meeting of the Board
     C: To: [email protected]
     C:
     C: Bill:
     C: The next meeting of the board of directors will be
     C: on Tuesday.
     C:                         John.
     C: .
     S: 250 OK
     C: QUIT
     S: 221 foo.com Service closing transmission channel

D.4 Verifying and Sending Scenario

     S: 220 foo.com Simple Mail Transfer Service Ready
     C: EHLO bar.com
     S: 250-foo.com greets bar.com
     S: 250-8BITMIME
     S: 250-SIZE
     S: 250-DSN



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RFC 2821             Simple Mail Transfer Protocol            April 2001


     S: 250-VRFY
     S: 250 HELP
     C: VRFY Crispin
     S: 250 Mark Crispin <[email protected]>
     C: SEND FROM:<[email protected]>
     S: 250 OK
     C: RCPT TO:<[email protected]>
     S: 250 OK
     C: DATA
     S: 354 Start mail input; end with <CRLF>.<CRLF>
     C: Blah blah blah...
     C: ...etc. etc. etc.
     C: .
     S: 250 OK
     C: QUIT
     S: 221 foo.com Service closing transmission channel

E. Other Gateway Issues

  In general, gateways between the Internet and other mail systems
  SHOULD attempt to preserve any layering semantics across the
  boundaries between the two mail systems involved.  Gateway-
  translation approaches that attempt to take shortcuts by mapping,
  (such as envelope information from one system to the message headers
  or body of another) have generally proven to be inadequate in
  important ways.  Systems translating between environments that do not
  support both envelopes and headers and Internet mail must be written
  with the understanding that some information loss is almost
  inevitable.

F. Deprecated Features of RFC 821

  A few features of RFC 821 have proven to be problematic and SHOULD
  NOT be used in Internet mail.

F.1 TURN

  This command, described in RFC 821, raises important security issues
  since, in the absence of strong authentication of the host requesting
  that the client and server switch roles, it can easily be used to
  divert mail from its correct destination.  Its use is deprecated;
  SMTP systems SHOULD NOT use it unless the server can authenticate the
  client.








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RFC 2821             Simple Mail Transfer Protocol            April 2001


F.2 Source Routing

  RFC 821 utilized the concept of explicit source routing to get mail
  from one host to another via a series of relays.  The requirement to
  utilize source routes in regular mail traffic was eliminated by the
  introduction of the domain name system "MX" record and the last
  significant justification for them was eliminated by the
  introduction, in RFC 1123, of a clear requirement that addresses
  following an "@" must all be fully-qualified domain names.
  Consequently, the only remaining justifications for the use of source
  routes are support for very old SMTP clients or MUAs and in mail
  system debugging.  They can, however, still be useful in the latter
  circumstance and for routing mail around serious, but temporary,
  problems such as problems with the relevant DNS records.

  SMTP servers MUST continue to accept source route syntax as specified
  in the main body of this document and in RFC 1123.  They MAY, if
  necessary, ignore the routes and utilize only the target domain in
  the address.  If they do utilize the source route, the message MUST
  be sent to the first domain shown in the address.  In particular, a
  server MUST NOT guess at shortcuts within the source route.

  Clients SHOULD NOT utilize explicit source routing except under
  unusual circumstances, such as debugging or potentially relaying
  around firewall or mail system configuration errors.

F.3 HELO

  As discussed in sections 3.1 and 4.1.1, EHLO is strongly preferred to
  HELO when the server will accept the former.  Servers must continue
  to accept and process HELO in order to support older clients.

F.4 #-literals

  RFC 821 provided for specifying an Internet address as a decimal
  integer host number prefixed by a pound sign, "#".  In practice, that
  form has been obsolete since the introduction of TCP/IP.  It is
  deprecated and MUST NOT be used.

F.5 Dates and Years

  When dates are inserted into messages by SMTP clients or servers
  (e.g., in trace fields), four-digit years MUST BE used.  Two-digit
  years are deprecated; three-digit years were never permitted in the
  Internet mail system.






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F.6 Sending versus Mailing

  In addition to specifying a mechanism for delivering messages to
  user's mailboxes, RFC 821 provided additional, optional, commands to
  deliver messages directly to the user's terminal screen.  These
  commands (SEND, SAML, SOML) were rarely implemented, and changes in
  workstation technology and the introduction of other protocols may
  have rendered them obsolete even where they are implemented.

  Clients SHOULD NOT provide SEND, SAML, or SOML as services.  Servers
  MAY implement them.  If they are implemented by servers, the
  implementation model specified in RFC 821 MUST be used and the
  command names MUST be published in the response to the EHLO command.






































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RFC 2821             Simple Mail Transfer Protocol            April 2001


Full Copyright Statement

  Copyright (C) The Internet Society (2001).  All Rights Reserved.

  This document and translations of it may be copied and furnished to
  others, and derivative works that comment on or otherwise explain it
  or assist in its implementation may be prepared, copied, published
  and distributed, in whole or in part, without restriction of any
  kind, provided that the above copyright notice and this paragraph are
  included on all such copies and derivative works.  However, this
  document itself may not be modified in any way, such as by removing
  the copyright notice or references to the Internet Society or other
  Internet organizations, except as needed for the purpose of
  developing Internet standards in which case the procedures for
  copyrights defined in the Internet Standards process must be
  followed, or as required to translate it into languages other than
  English.

  The limited permissions granted above are perpetual and will not be
  revoked by the Internet Society or its successors or assigns.

  This document and the information contained herein is provided on an
  "AS IS" basis and THE INTERNET SOCIETY AND THE INTERNET ENGINEERING
  TASK FORCE DISCLAIMS ALL WARRANTIES, EXPRESS OR IMPLIED, INCLUDING
  BUT NOT LIMITED TO ANY WARRANTY THAT THE USE OF THE INFORMATION
  HEREIN WILL NOT INFRINGE ANY RIGHTS OR ANY IMPLIED WARRANTIES OF
  MERCHANTABILITY OR FITNESS FOR A PARTICULAR PURPOSE.

Acknowledgement

  Funding for the RFC Editor function is currently provided by the
  Internet Society.



















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