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PROPOSED STANDARD
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Network Working Group                                 R. Siemborski, Ed.Request for Comments: 4954                                  Google, Inc.Obsoletes:2554                                         A. Melnikov, Ed.Updates:3463                                              Isode LimitedCategory: Standards Track                                      July 2007SMTP Service Extension for AuthenticationStatus 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 IETF Trust (2007).Abstract   This document defines a Simple Mail Transport Protocol (SMTP)   extension whereby an SMTP client may indicate an authentication   mechanism to the server, perform an authentication protocol exchange,   and optionally negotiate a security layer for subsequent protocol   interactions during this session.  This extension includes a profile   of the Simple Authentication and Security Layer (SASL) for SMTP.   This document obsoletesRFC 2554.Siemborski & Melnikov       Standards Track                     [Page 1]

RFC 4954       SMTP Service Extension for Authentication       July 2007Table of Contents1. Introduction ....................................................22. How to Read This Document .......................................23. The Authentication Service Extension ............................34. The AUTH Command ................................................34.1. Examples ...................................................75. The AUTH Parameter to the MAIL FROM command .....................95.1. Examples ..................................................106. Status Codes ...................................................117. Additional requirements on servers .............................128. Formal Syntax ..................................................139. Security Considerations ........................................1410. IANA Considerations ...........................................1511. Normative References ..........................................1512. Informative References ........................................1613. Acknowledgments ...............................................1714. Additional Requirements When Using SASL PLAIN over TLS ........1715. Changes sinceRFC 2554 ........................................181.  Introduction   This document defines a Simple Mail Transport Protocol (SMTP)   extension whereby an SMTP client may indicate an authentication   mechanism to the server, perform an authentication protocol exchange,   optionally negotiate a security layer for subsequent protocol   interactions during this session and, during a mail transaction,   optionally specify a mailbox associated with the identity that   submitted the message to the mail delivery system.   This extension includes a profile of the Simple Authentication and   Security Layer (SASL) for SMTP.   When compared toRFC 2554, this document deprecates use of the 538   response code, adds a new Enhanced Status Code, adds a requirement to   support SASLprep profile for preparing authorization identities,   recommends use ofRFC 3848 transmission types in the Received trace   header field, and clarifies interaction with SMTP PIPELINING   [PIPELINING] extension.2.  How to Read This Document   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 in [KEYWORDS].   In examples, "C:" and "S:" indicate lines sent by the client and   server, respectively.Siemborski & Melnikov       Standards Track                     [Page 2]

RFC 4954       SMTP Service Extension for Authentication       July 20073.  The Authentication Service Extension   1.  The name of this [SMTP] service extension is "Authentication".   2.  The EHLO keyword value associated with this extension is "AUTH".   3.  The AUTH EHLO keyword contains as a parameter a space-separated       list of the names of available [SASL] mechanisms.  The list of       available mechanisms MAY change after a successful STARTTLS       command [SMTP-TLS].   4.  A new [SMTP] verb "AUTH" is defined.   5.  An optional parameter using the keyword "AUTH" is added to the       MAIL FROM command, and extends the maximum line length of the       MAIL FROM command by 500 characters.   6.  This extension is appropriate for the submission protocol       [SUBMIT].4.  The AUTH Command   AUTH mechanism [initial-response]      Arguments:          mechanism: A string identifying a [SASL] authentication          mechanism.          initial-response: An optional initial client response.  If          present, this response MUST be encoded as described inSection4 of [BASE64] or contain a single character "=".      Restrictions:          After an AUTH command has been successfully completed, no more          AUTH commands may be issued in the same session.  After a          successful AUTH command completes, a server MUST reject any          further AUTH commands with a 503 reply.          The AUTH command is not permitted during a mail transaction.          An AUTH command issued during a mail transaction MUST be          rejected with a 503 reply.      Discussion:          The AUTH command initiates a [SASL] authentication exchange          between the client and the server.  The client identifies the          SASL mechanism to use with the first parameter of the AUTH          command.  If the server supports the requested authentication          mechanism, it performs the SASL exchange to authenticate theSiemborski & Melnikov       Standards Track                     [Page 3]

RFC 4954       SMTP Service Extension for Authentication       July 2007          user.  Optionally, it also negotiates a security layer for          subsequent protocol interactions during this session.  If the          requested authentication mechanism is invalid (e.g., is not          supported or requires an encryption layer), the server rejects          the AUTH command with a 504 reply.  If the server supports the          [ESMTP-CODES] extension, it SHOULD return a 5.5.4 enhanced          response code.          The SASL authentication exchange consists of a series of          server challenges and client responses that are specific to          the chosen [SASL] mechanism.          A server challenge is sent as a 334 reply with the text part          containing the [BASE64] encoded string supplied by the SASL          mechanism.  This challenge MUST NOT contain any text other          than the BASE64 encoded challenge.          A client response consists of a line containing a [BASE64]          encoded string.  If the client wishes to cancel the          authentication exchange, it issues a line with a single "*".          If the server receives such a response, it MUST reject the          AUTH command by sending a 501 reply.          The optional initial response argument to the AUTH command is          used to save a round-trip when using authentication mechanisms          that support an initial client response.  If the initial          response argument is omitted and the chosen mechanism requires          an initial client response, the server MUST proceed as defined          in Section 5.1 of [SASL].  In SMTP, a server challenge that          contains no data is defined as a 334 reply with no text part.          Note that there is still a space following the reply code, so          the complete response line is "334 ".          Note that the AUTH command is still subject to the line length          limitations defined in [SMTP].  If use of the initial response          argument would cause the AUTH command to exceed this length,          the client MUST NOT use the initial response parameter (and          instead proceed as defined in Section 5.1 of [SASL]).          If the client is transmitting an initial response of zero          length, it MUST instead transmit the response as a single          equals sign ("=").  This indicates that the response is          present, but contains no data.          If the client uses an initial-response argument to the AUTH          command with a SASL mechanism in which the client does not          begin the authentication exchange, the server MUST reject theSiemborski & Melnikov       Standards Track                     [Page 4]

RFC 4954       SMTP Service Extension for Authentication       July 2007          AUTH command with a 501 reply.  Servers using the enhanced          status codes extension [ESMTP-CODES] SHOULD return an enhanced          status code of 5.7.0 in this case.          If the server cannot [BASE64] decode any client response, it          MUST reject the AUTH command with a 501 reply (and an enhanced          status code of 5.5.2).  If the client cannot BASE64 decode any          of the server's challenges, it MUST cancel the authentication          using the "*" response.  In particular, servers and clients          MUST reject (and not ignore) any character not explicitly          allowed by the BASE64 alphabet, and MUST reject any sequence          of BASE64 characters that contains the pad character ('=')          anywhere other than the end of the string (e.g., "=AAA" and          "AAA=BBB" are not allowed).          Note that these [BASE64] strings can be much longer than          normal SMTP commands.  Clients and servers MUST be able to          handle the maximum encoded size of challenges and responses          generated by their supported authentication mechanisms.  This          requirement is independent of any line length limitations the          client or server may have in other parts of its protocol          implementation.  (At the time of writing of this document,          12288 octets is considered to be a sufficient line length          limit for handling of deployed authentication mechanisms.)          If, during an authentication exchange, the server receives a          line that is longer than the server's authentication buffer,          the server fails the AUTH command with the 500 reply.  Servers          using the enhanced status codes extension [ESMTP-CODES] SHOULD          return an enhanced status code of 5.5.6 in this case.          The authorization identity generated by this [SASL] exchange          is a "simple username" (in the sense defined in [SASLprep]),          and both client and server SHOULD (*) use the [SASLprep]          profile of the [StringPrep] algorithm to prepare these names          for transmission or comparison.  If preparation of the          authorization identity fails or results in an empty string          (unless it was transmitted as the empty string), the server          MUST fail the authentication.      (*) Note: Future revision of this specification may change this      requirement to MUST.  Currently, the SHOULD is used in order to      avoid breaking the majority of existing implementations.   If the server is unable to authenticate the client, it SHOULD reject   the AUTH command with a 535 reply unless a more specific error code   is appropriate.  Should the client successfully complete the   exchange, the SMTP server issues a 235 reply.  (Note that the SMTP   protocol doesn't support the SASL feature of returning additionalSiemborski & Melnikov       Standards Track                     [Page 5]

RFC 4954       SMTP Service Extension for Authentication       July 2007   data with a successful outcome.)  These status codes, along with   others defined by this extension, are discussed inSection 6 of this   document.   If a security layer is negotiated during the SASL exchange, it takes   effect for the client on the octet immediately following the CRLF   that concludes the last response generated by the client.  For the   server, it takes effect immediately following the CRLF of its success   reply.   When a security layer takes effect, the SMTP protocol is reset to the   initial state (the state in SMTP after a server issues a 220 service   ready greeting).  The server MUST discard any knowledge obtained from   the client, such as the EHLO argument, which was not obtained from   the SASL negotiation itself.  Likewise, the client MUST discard any   knowledge obtained from the server, such as the list of SMTP service   extensions, which was not obtained from the SASL negotiation itself.   (Note that a client MAY compare the advertised SASL mechanisms before   and after authentication in order to detect an active down-   negotiation attack).   The client SHOULD send an EHLO command as the first command after a   successful SASL negotiation that results in the enabling of a   security layer.   When an entity (whether it is the client or the server end) is   sending data, and both [TLS] and SASL security layers are in effect,   the TLS encoding MUST be applied after the SASL encoding, regardless   of the order in which the layers were negotiated.   The service name specified by this protocol's profile of SASL is   "smtp".  This service name is also to be used for the [SUBMIT]   protocol.   If an AUTH command fails, the client MAY proceed without   authentication.  Alternatively, the client MAY try another   authentication mechanism or present different credentials by issuing   another AUTH   Note: A server implementation MUST implement a configuration in which   it does NOT permit any plaintext password mechanisms, unless either   the STARTTLS [SMTP-TLS] command has been negotiated or some other   mechanism that protects the session from password snooping has been   provided.  Server sites SHOULD NOT use any configuration which   permits a plaintext password mechanism without such a protection   mechanism against password snooping.Siemborski & Melnikov       Standards Track                     [Page 6]

RFC 4954       SMTP Service Extension for Authentication       July 2007   To ensure interoperability, client and server implementations of this   extension MUST implement the [PLAIN] SASL mechanism running over TLS   [TLS] [SMTP-TLS].  See alsoSection 15 for additional requirements on   implementations of [PLAIN] over [TLS].   Note that many existing client and server implementations implement   CRAM-MD5 [CRAM-MD5] SASL mechanism.  In order to ensure   interoperability with deployed software, new implementations MAY   implement it; however, implementations should be aware that this SASL   mechanism doesn't provide any server authentication.  Note that at   the time of writing of this document the SASL Working Group is   working on several replacement SASL mechanisms that provide server   authentication and other features.   When the AUTH command is used together with the [PIPELINING]   extension, it MUST be the last command in a pipelined group of   commands.  The only exception to this rule is when the AUTH command   contains an initial response for a SASL mechanism that allows the   client to send data first, the SASL mechanism is known to complete in   one round-trip, and a security layer is not negotiated by the client.   Two examples of such SASL mechanisms are PLAIN [PLAIN] and EXTERNAL   [SASL].4.1. Examples   Here is an example of a client attempting AUTH using the [PLAIN] SASL   mechanism under a TLS layer, and making use of the initial client   response:   S: 220-smtp.example.com ESMTP Server   C: EHLO client.example.com   S: 250-smtp.example.com Hello client.example.com   S: 250-AUTH GSSAPI DIGEST-MD5   S: 250-ENHANCEDSTATUSCODES   S: 250 STARTTLS   C: STARTTLS   S: 220 Ready to start TLS     ... TLS negotiation proceeds, further commands         protected by TLS layer ...   C: EHLO client.example.com   S: 250-smtp.example.com Hello client.example.com   S: 250 AUTH GSSAPI DIGEST-MD5 PLAIN   C: AUTH PLAIN dGVzdAB0ZXN0ADEyMzQ=   S: 235 2.7.0 Authentication successful   Here is another client that is attempting AUTH PLAIN under a TLS   layer, this time without the initial response.  Parts of the   negotiation before the TLS layer was established have been omitted:Siemborski & Melnikov       Standards Track                     [Page 7]

RFC 4954       SMTP Service Extension for Authentication       July 2007     ... TLS negotiation proceeds, further commands         protected by TLS layer ...   C: EHLO client.example.com   S: 250-smtp.example.com Hello client.example.com   S: 250 AUTH GSSAPI DIGEST-MD5 PLAIN   C: AUTH PLAIN    (note: there is a single space following the 334     on the following line)   S: 334   C: dGVzdAB0ZXN0ADEyMzQ=   S: 235 2.7.0 Authentication successful   Here is an example using CRAM-MD5 [CRAM-MD5], a mechanism in which   the client does not begin the authentication exchange, and includes a   server challenge:   S: 220-smtp.example.com ESMTP Server   C: EHLO client.example.com   S: 250-smtp.example.com Hello client.example.com   S: 250-AUTH DIGEST-MD5 CRAM-MD5   S: 250-ENHANCEDSTATUSCODES   S: 250 STARTTLS   C: AUTH CRAM-MD5   S: 334 PDQxOTI5NDIzNDEuMTI4Mjg0NzJAc291cmNlZm91ci5hbmRyZXcuY211LmVk      dT4=   C: cmpzMyBlYzNhNTlmZWQzOTVhYmExZWM2MzY3YzRmNGI0MWFjMA==   S: 235 2.7.0 Authentication successful   Here is an example of a client attempting AUTH EXTERNAL under TLS,   using the derived authorization ID (and thus a zero-length initial   client response).   S: 220-smtp.example.com ESMTP Server   C: EHLO client.example.com   S: 250-smtp.example.com Hello client.example.com   S: 250-AUTH GSSAPI DIGEST-MD5   S: 250-ENHANCEDSTATUSCODES   S: 250 STARTTLS   C: STARTTLS   S: 220 Ready to start TLS     ... TLS negotiation proceeds, further commands         protected by TLS layer ...   C: EHLO client.example.com   S: 250-smtp.example.com Hello client.example.com   S: 250 AUTH EXTERNAL GSSAPI DIGEST-MD5 PLAIN   C: AUTH EXTERNAL =   S: 235 2.7.0 Authentication successfulSiemborski & Melnikov       Standards Track                     [Page 8]

RFC 4954       SMTP Service Extension for Authentication       July 20075.  The AUTH Parameter to the MAIL FROM command   AUTH=mailbox   Arguments:        A <mailbox> (see Section 4.1.2 of [SMTP]) that is associated        with the identity that submitted the message to the delivery        system, or the two character sequence "<>" indicating such an        identity is unknown or insufficiently authenticated.  To comply        with restrictions imposed on ESMTP parameters, the <mailbox> is        encoded inside an xtext.  The syntax of an xtext is described in        Section 4 of [ESMTP-DSN].   Note:        For the purposes of this discussion, "authenticated identity"        refers to the identity (if any) derived from the authorization        identity of previous AUTH command, while the terms "authorized        identity" and "supplied <mailbox>" refer to the sender identity        that is being associated with a particular message.  Note that        one authenticated identity may be able to identify messages as        being sent by any number of authorized identities within a        single session.  For example, this may be the case when an SMTP        server (one authenticated identity) is processing its queue        (many messages with distinct authorized identities).   Discussion:        The optional AUTH parameter to the MAIL FROM command allows        cooperating agents in a trusted environment to communicate the        authorization identity associated with individual messages.        If the server trusts the authenticated identity of the client to        assert that the message was originally submitted by the supplied        <mailbox>, then the server SHOULD supply the same <mailbox> in        an AUTH parameter when relaying the message to any other server        which supports the AUTH extension.        For this reason, servers that advertise support for this        extension MUST support the AUTH parameter to the MAIL FROM        command even when the client has not authenticated itself to the        server.        A MAIL FROM parameter of AUTH=<> indicates that the original        submitter of the message is not known.  The server MUST NOT        treat the message as having been originally submitted by the        authenticated identity that resulted from the AUTH command.Siemborski & Melnikov       Standards Track                     [Page 9]

RFC 4954       SMTP Service Extension for Authentication       July 2007        If the AUTH parameter to the MAIL FROM command is not supplied,        the client has authenticated, and the server believes the        message is an original submission, the server MAY generate a        <mailbox> from the user's authenticated identity for use in an        AUTH parameter when relaying the message to any server which        supports the AUTH extension.  The generated <mailbox> is        implementation specific, but it MUST conform to the syntax of        [SMTP].  If the implementation cannot generate a valid        <mailbox>, it MUST transmit AUTH=<> when relaying this message.        If the server does not sufficiently trust the authenticated        identity of the client, or if the client is not authenticated,        then the server MUST behave as if the AUTH=<> parameter was        supplied.  The server MAY, however, write the value of any        supplied AUTH parameter to a log file.        If an AUTH=<> parameter was supplied, either explicitly or due        to the requirement in the previous paragraph, then the server        MUST supply the AUTH=<> parameter when relaying the message to        any server which it has authenticated to using the AUTH        extension.        A server MAY treat expansion of a mailing list as a new        submission, setting the AUTH parameter to the mailing list        address or mailing list administration address when relaying the        message to list subscribers.        Note that an implementation which is hard-coded to treat all        clients as being insufficiently trusted is compliant with this        specification.  In that case, the implementation does nothing        more than parse and discard syntactically valid AUTH parameters        to the MAIL FROM command, and supply AUTH=<> parameters to any        servers that it authenticates to.5.1.  Examples   An example where the original identity of the sender is trusted and   known:   C: MAIL FROM:<e=mc2@example.com> AUTH=e+3Dmc2@example.com   S: 250 OK   One example where the identity of the sender is not trusted or is   otherwise being suppressed by the client:   C: MAIL FROM:<john+@example.org> AUTH=<>   S: 250 OKSiemborski & Melnikov       Standards Track                    [Page 10]

RFC 4954       SMTP Service Extension for Authentication       July 20076.  Status Codes   The following error codes may be used to indicate various success or   failure conditions.  Servers that return enhanced status codes   [ESMTP-CODES] SHOULD use the enhanced codes suggested here.   235 2.7.0  Authentication Succeeded   This response to the AUTH command indicates that the authentication   was successful.   432 4.7.12  A password transition is needed   This response to the AUTH command indicates that the user needs to   transition to the selected authentication mechanism.  This is   typically done by authenticating once using the [PLAIN]   authentication mechanism.  The selected mechanism SHOULD then work   for authentications in subsequent sessions.   454 4.7.0  Temporary authentication failure   This response to the AUTH command indicates that the authentication   failed due to a temporary server failure.  The client SHOULD NOT   prompt the user for another password in this case, and should instead   notify the user of server failure.   534 5.7.9  Authentication mechanism is too weak   This response to the AUTH command indicates that the selected   authentication mechanism is weaker than server policy permits for   that user.  The client SHOULD retry with a new authentication   mechanism.   535 5.7.8  Authentication credentials invalid   This response to the AUTH command indicates that the authentication   failed due to invalid or insufficient authentication credentials.  In   this case, the client SHOULD ask the user to supply new credentials   (such as by presenting a password dialog box).   500 5.5.6  Authentication Exchange line is too long   This response to the AUTH command indicates that the authentication   failed due to the client sending a [BASE64] response that is longer   than the maximum buffer size available for the currently selected   SASL mechanism.Siemborski & Melnikov       Standards Track                    [Page 11]

RFC 4954       SMTP Service Extension for Authentication       July 2007   530 5.7.0  Authentication required   This response SHOULD be returned by any command other than AUTH,   EHLO, HELO, NOOP, RSET, or QUIT when server policy requires   authentication in order to perform the requested action and   authentication is not currently in force.   538 5.7.11  Encryption required for requested authentication               mechanism   This response to the AUTH command indicates that the selected   authentication mechanism may only be used when the underlying SMTP   connection is encrypted.  Note that this response code is documented   here for historical purposes only.  Modern implementations SHOULD NOT   advertise mechanisms that are not permitted due to lack of   encryption, unless an encryption layer of sufficient strength is   currently being employed.   This document adds several new enhanced status codes to the list   defined in [ENHANCED]:   The following 3 Enhanced Status Codes were defined above:       5.7.8 Authentication credentials invalid       5.7.9 Authentication mechanism is too weak       5.7.11 Encryption required for requested authentication mechanism   X.5.6     Authentication Exchange line is too long   This enhanced status code SHOULD be returned when the server fails   the AUTH command due to the client sending a [BASE64] response which   is longer than the maximum buffer size available for the currently   selected SASL mechanism.  This is useful for both permanent and   persistent transient errors.7.  Additional Requirements on Servers   As described in Section 4.4 of [SMTP], an SMTP server that receives a   message for delivery or further processing MUST insert the   "Received:" header field at the beginning of the message content.   This document places additional requirements on the content of a   generated "Received:" header field.  Upon successful authentication,   a server SHOULD use the "ESMTPA" or the "ESMTPSA" [SMTP-TT] (when   appropriate) keyword in the "with" clause of the Received header   field.Siemborski & Melnikov       Standards Track                    [Page 12]

RFC 4954       SMTP Service Extension for Authentication       July 20078.  Formal Syntax   The following syntax specification uses the Augmented Backus-Naur   Form notation as specified in [ABNF].  Non-terminals referenced but   not defined below are as defined by [ABNF] or [SASL].  The non-   terminal <mailbox> is defined in [SMTP].   Except as noted otherwise, all alphabetic characters are case-   insensitive.  The use of upper or lower case characters to define   token strings is for editorial clarity only.  Implementations MUST   accept these strings in a case-insensitive fashion.      hexchar         = "+" HEXDIG HEXDIG      xchar           = %x21-2A / %x2C-3C / %x3E-7E                        ;; US-ASCII except for "+", "=", SP, and CTL      xtext           = *(xchar / hexchar)                        ;; non-US-ASCII is only allowed as hexchar      auth-command    = "AUTH" SP sasl-mech [SP initial-response]                        *(CRLF [base64]) [CRLF cancel-response]                        CRLF                        ;; <sasl-mech> is defined in [SASL]      auth-param      = "AUTH=" xtext                        ;; Parameter to the MAIL FROM command.                        ;; This non-terminal complies with                        ;; syntax defined by esmtp-param [SMTP].                        ;;                        ;; The decoded form of the xtext MUST be                        ;; either a <mailbox> or the two                        ;; characters "<>"      base64          = base64-terminal /                        ( 1*(4base64-char) [base64-terminal] )      base64-char     = ALPHA / DIGIT / "+" / "/"                        ;; Case-sensitive      base64-terminal = (2base64-char "==") / (3base64-char "=")      continue-req    = "334" SP [base64] CRLF                        ;; Intermediate response to the AUTH                        ;; command.                        ;; This non-terminal complies with                        ;; syntax defined by Reply-line [SMTP].Siemborski & Melnikov       Standards Track                    [Page 13]

RFC 4954       SMTP Service Extension for Authentication       July 2007      initial-response= base64 / "="      cancel-response = "*"9.  Security Considerations   Security issues are discussed throughout this memo.   If a client uses this extension to get an encrypted tunnel through an   insecure network to a cooperating server, it needs to be configured   to never send mail to that server when the connection is not mutually   authenticated and encrypted.  Otherwise, an attacker could steal the   client's mail by hijacking the [SMTP] connection and either   pretending the server does not support the Authentication extension   or causing all AUTH commands to fail.   Before the [SASL] negotiation has begun, any protocol interactions   are performed in the clear and may be modified by an active attacker.   For this reason, clients and servers MUST discard any knowledge   obtained prior to the start of the SASL negotiation upon the   establishment of a security layer.   This mechanism does not protect the TCP port, so an active attacker   may redirect a relay connection attempt (i.e., a connection between   two Mail Transfer Agents (MTAs)) to the submission port [SUBMIT].   The AUTH=<> parameter prevents such an attack from causing a relayed   message and, in the absence of other envelope authentication, from   picking up the authentication of the relay client.   A message submission client may require the user to authenticate   whenever a suitable [SASL] mechanism is advertised.  Therefore, it   may not be desirable for a submission server [SUBMIT] to advertise a   SASL mechanism when use of that mechanism grants the clients no   benefits over anonymous submission.   Servers MAY implement a policy whereby the connection is dropped   after a number of failed authentication attempts.  If they do so,   they SHOULD NOT drop the connection until at least 3 attempts to   authenticate have failed.   If an implementation supports SASL mechanisms that are vulnerable to   passive eavesdropping attacks (such as [PLAIN]), then the   implementation MUST support at least one configuration where these   SASL mechanisms are not advertised or used without the presence of an   external security layer such as [TLS].Siemborski & Melnikov       Standards Track                    [Page 14]

RFC 4954       SMTP Service Extension for Authentication       July 2007   This extension is not intended to replace or be used instead of end-   to-end message signature and encryption systems such as [S/MIME] or   [PGP].  This extension addresses a different problem than end-to-end   systems; it has the following key differences:   1.  It is generally useful only within a trusted enclave.   2.  It protects the entire envelope of a message, not just the       message's body.   3.  It authenticates the message submission, not authorship of the       message content.   4.  When mutual authentication is used along with a security layer,       it can give the sender some assurance that the message was       successfully delivered to the next hop.   Additional security considerations are mentioned in the [SASL]   specification.  Additional security considerations specific to a   particular SASL mechanism are described in the relevant   specification.  Additional security considerations for [PLAIN] over   [TLS] are mentioned inSection 15 of this document.10.  IANA Considerations   IANA updated the entry for the "smtp" SASL protocol name to point at   this document.   IANA updated the registration of the Authentication SMTP service   extension as defined inSection 3 of this document.  This registry is   currently located at <http://www.iana.org/assignments/mail-parameters>.11.  Normative References   [ABNF]        Crocker, D. and P. Overell, "Augmented BNF for Syntax                 Specifications: ABNF",RFC 4234, October 2005.   [BASE64]      Josefsson, S., "The Base16, Base32, and Base64 Data                 Encodings",RFC 4648, October 2006.   [ESMTP-CODES] Freed, N., "SMTP Service Extension for Returning                 Enhanced Error Codes",RFC 2034, October 1996.   [ENHANCED]    Vaudreuil, G., "Enhanced Mail System Status Codes",RFC3463, January 2003.Siemborski & Melnikov       Standards Track                    [Page 15]

RFC 4954       SMTP Service Extension for Authentication       July 2007   [ESMTP-DSN]   Moore, K., "Simple Mail Transfer Protocol (SMTP)                 Service Extension Delivery Status Notifications                 (DSNs)",RFC 3461, January 2003.   [KEYWORDS]    Bradner, S., "Key words for use in RFCs to Indicate                 Requirement Levels",BCP 14,RFC 2119, March 1997.   [SASL]        Melnikov, A. and K. Zeilenga, "Simple Authentication                 and Security Layer (SASL)",RFC 4422, June 2006.   [SASLprep]    Zeilenga, K., "SASLprep: Stringprep Profile for User                 Names and Passwords",RFC 4013, February 2005.   [SMTP]        Klensin, J., "Simple Mail Transfer Protocol",RFC 2821,                 April 2001.   [SMTP-TLS]    Hoffman, P., "SMTP Service Extension for Secure SMTP                 over Transport Layer Security",RFC 3207, February                 2002.   [StringPrep]  Hoffman, P. and M. Blanchet, "Preparation of                 Internationalized Strings ("stringprep")",RFC 3454,                 December 2002.   [SUBMIT]      Gellens, R. and J. Klensin, "Message Submission for                 Mail",RFC 4409, April 2006.   [SMTP-TT]     Newman, C., "ESMTP and LMTP Transmission Types                 Registration",RFC 3848, July 2004.   [PLAIN]       Zeilenga, K., Ed., "The PLAIN Simple Authentication and                 Security Layer (SASL) Mechanism",RFC 4616, August                 2006.   [X509]        Housley, R., Polk, W., Ford, W., and D. Solo, "Internet                 X.509 Public Key Infrastructure Certificate and                 Certificate Revocation List (CRL) Profile",RFC 3280,                 April 2002.12.  Informative References   [PGP]         Elkins, M., "MIME Security with Pretty Good Privacy                 (PGP)",RFC 2015, October 1996.   [S/MIME]      Ramsdell, B., Ed., "Secure/Multipurpose Internet Mail                 Extensions (S/MIME) Version 3.1 Message Specification",RFC 3851, July 2004.Siemborski & Melnikov       Standards Track                    [Page 16]

RFC 4954       SMTP Service Extension for Authentication       July 2007   [TLS]         Dierks, T. and E. Rescorla, "The Transport Layer                 Security (TLS) Protocol Version 1.1",RFC 4346, April                 2006.   [PIPELINING]  Freed, N., "SMTP Service Extension for Command                 Pipelining", STD 60,RFC 2920, September 2000.   [CRAM-MD5]    Klensin, J., Catoe, R., and P. Krumviede, "IMAP/POP                 AUTHorize Extension for Simple Challenge/Response",RFC2195, September 1997.13.  Acknowledgments   The editors would like to acknowledge the contributions of John Myers   and other contributors toRFC 2554, on which this document draws from   heavily.   The editors would also like to thank Ken Murchison, Mark Crispin,   Chris Newman, David Wilson, Dave Cridland, Frank Ellermann, Ned   Freed, John Klensin, Tony Finch, Abhijit Menon-Sen, Philip Guenther,   Sam Hartman, Russ Housley, Cullen Jennings, and Lisa Dusseault for   the time they devoted to reviewing of this document and/or for the   comments received.14.  Additional Requirements When Using SASL PLAIN over TLS   This section is normative for SMTP implementations that support SASL   [PLAIN] over [TLS].   If an SMTP client is willing to use SASL PLAIN over TLS to   authenticate to the SMTP server, the client verifies the server   certificate according to the rules of [X509].  If the server has not   provided any certificate, or if the certificate verification fails,   the client MUST NOT attempt to authenticate using the SASL PLAIN   mechanism.   After a successful [TLS] negotiation, the client MUST check its   understanding of the server hostname against the server's identity as   presented in the server Certificate message, in order to prevent   man-in-the-middle attacks.  If the match fails, the client MUST NOT   attempt to authenticate using the SASL PLAIN mechanism.  Matching is   performed according to the following rules:        The client MUST use the server hostname it used to open the        connection as the value to compare against the server name as        expressed in the server certificate.  The client MUST NOT useSiemborski & Melnikov       Standards Track                    [Page 17]

RFC 4954       SMTP Service Extension for Authentication       July 2007        any form of the server hostname derived from an insecure remote        source (e.g., insecure DNS lookup).  CNAME canonicalization is        not done.        If a subjectAltName extension of type dNSName is present in the        certificate, it SHOULD be used as the source of the server's        identity.        Matching is case-insensitive.        A "*" wildcard character MAY be used as the leftmost name        component in the certificate.  For example, *.example.com would        match a.example.com, foo.example.com, etc., but would not match        example.com.        If the certificate contains multiple names (e.g., more than one        dNSName field), then a match with any one of the fields is        considered acceptable.15.  Changes sinceRFC 2554   1.  Clarified that servers MUST support the use of the AUTH=mailbox       parameter to MAIL FROM, even when the client is not       authenticated.   2.  Clarified the initial-client-send requirements, and give       additional examples.   3.  Updated references to newer versions of various specifications.   4.  Required SASL PLAIN (over TLS) as mandatory-to-implement.   5.  Clarified that the mechanism list can change.   6.  Deprecated the use of the 538 response code.   7.  Added the use of the SASLprep profile for preparing authorization       identities.   8.  Substantial cleanup of response codes and indicated suggested       enhanced response codes.  Also indicated what response codes       should result in a client prompting the user for new credentials.   9.  Updated ABNF section to useRFC 4234.   10. Clarified interaction with SMTP PIPELINING extension.   11. Added a reference toRFC 3848.Siemborski & Melnikov       Standards Track                    [Page 18]

RFC 4954       SMTP Service Extension for Authentication       July 2007   12. Added a new Enhanced Status Code for "authentication line too       long" case.   13. Other general editorial clarifications.Editors' Addresses   Robert Siemborski   Google, Inc.   1600 Ampitheatre Parkway   Mountain View, CA 94043, USA   Phone: +1 650 623 6925   EMail: robsiemb@google.com   Alexey Melnikov   Isode Limited   5 Castle Business Village, 36 Station Road,   Hampton, Middlesex, TW12 2BX, UK   EMail: Alexey.Melnikov@isode.comSiemborski & Melnikov       Standards Track                    [Page 19]

RFC 4954       SMTP Service Extension for Authentication       July 2007Full Copyright Statement   Copyright (C) The IETF Trust (2007).   This document is subject to the rights, licenses and restrictions   contained inBCP 78, and except as set forth therein, the authors   retain all their rights.   This document and the information contained herein are provided on an   "AS IS" basis and THE CONTRIBUTOR, THE ORGANIZATION HE/SHE REPRESENTS   OR IS SPONSORED BY (IF ANY), THE INTERNET SOCIETY, THE IETF TRUST AND   THE INTERNET ENGINEERING TASK FORCE DISCLAIM 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.Intellectual Property   The IETF takes no position regarding the validity or scope of any   Intellectual Property Rights or other rights that might be claimed to   pertain to the implementation or use of the technology described in   this document or the extent to which any license under such rights   might or might not be available; nor does it represent that it has   made any independent effort to identify any such rights.  Information   on the procedures with respect to rights in RFC documents can be   found inBCP 78 andBCP 79.   Copies of IPR disclosures made to the IETF Secretariat and any   assurances of licenses to be made available, or the result of an   attempt made to obtain a general license or permission for the use of   such proprietary rights by implementers or users of this   specification can be obtained from the IETF on-line IPR repository athttp://www.ietf.org/ipr.   The IETF invites any interested party to bring to its attention any   copyrights, patents or patent applications, or other proprietary   rights that may cover technology that may be required to implement   this standard.  Please address the information to the IETF at   ietf-ipr@ietf.org.Acknowledgement   Funding for the RFC Editor function is currently provided by the   Internet Society.Siemborski & Melnikov       Standards Track                    [Page 20]

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