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:

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 <jsmith@foo.com>
553-Harry Smith <hsmith@foo.com>
553 Melvin Smith <dweep@foo.com>

or

553-Ambiguous; Possibilities
553- <jsmith@foo.com>
553- <hsmith@foo.com>
553 <dweep@foo.com>

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 <Postel@isi.edu>
S: 250-Fred Fonebone <Fonebone@physics.foo-u.edu>
S: 250 Sam Q. Smith <SQSmith@specific.generic.com>

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:<userx@y.foo.org>
RCPT TO:<@hosta.int,@jkl.org:userc@d.bar.org>

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

MAIL FROM:<userx@y.foo.org>
RCPT TO:<userc@d.bar.org>

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

MAIL FROM:<userx@y.foo.org>
RCPT TO:<@hosta.int,@jkl.org:userc@d.bar.org>

or to jkl.org, using the envelope commands

MAIL FROM:<userx@y.foo.org>
RCPT TO:<@jkl.org:userc@d.bar.org>

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 = http://www.mamicode.com/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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[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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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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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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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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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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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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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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- 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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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: klensin@research.att.com

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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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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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:<Smith@bar.com>
S: 250 OK
C: RCPT TO:<Jones@foo.com>
S: 250 OK
C: RCPT TO:<Green@foo.com>
S: 550 No such user here
C: RCPT TO:<Brown@foo.com>

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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:<Smith@bar.com>
S: 250 OK
C: RCPT TO:<Jones@foo.com>
S: 250 OK
C: RCPT TO:<Green@foo.com>
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:<JQP@bar.com>
S: 250 OK
C: RCPT TO:<@foo.com:Jones@XYZ.COM>
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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C: From: John Q. Public <JQP@bar.com>
C: Subject: The Next Meeting of the Board
C: To: Jones@xyz.com
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:JQP@bar.com>
S: 250 OK
C: RCPT TO:<Jones@XYZ.COM>
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 <JQP@bar.com>
C: Subject: The Next Meeting of the Board
C: To: Jones@xyz.com
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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S: 250-VRFY
S: 250 HELP
C: VRFY Crispin
S: 250 Mark Crispin <Admin.MRC@foo.com>
C: SEND FROM:<EAK@bar.com>
S: 250 OK
C: RCPT TO:<Admin.MRC@foo.com>
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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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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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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smtp