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+Network Working Group                                     P. Hoffman
+Request for Comments: 2487                  Internet Mail Consortium
+Category: Standards Track                               January 1999
+
+
+            SMTP Service Extension for Secure SMTP over TLS
+
+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 (1999).  All Rights Reserved.
+
+1. Abstract
+
+   This document describes an extension to the SMTP service that allows
+   an SMTP server and client to use transport-layer security to provide
+   private, authenticated communication over the Internet. This gives
+   SMTP agents the ability to protect some or all of their
+   communications from eavesdroppers and attackers.
+
+2. Introduction
+
+   SMTP [RFC-821] servers and clients normally communicate in the clear
+   over the Internet. In many cases, this communication goes through one
+   or more router that is not controlled or trusted by either entity.
+   Such an untrusted router might allow a third party to monitor or
+   alter the communications between the server and client.
+
+   Further, there is often a desire for two SMTP agents to be able to
+   authenticate each others' identities. For example, a secure SMTP
+   server might only allow communications from other SMTP agents it
+   knows, or it might act differently for messages received from an
+   agent it knows than from one it doesn't know.
+
+   TLS [TLS], more commonly known as SSL, is a popular mechanism for
+   enhancing TCP communications with privacy and authentication. TLS is
+   in wide use with the HTTP protocol, and is also being used for adding
+   security to many other common protocols that run over TCP.
+
+
+
+
+
+
+Hoffman                     Standards Track                     [Page 1]
+
+RFC 2487                 SMTP Service Extension             January 1999
+
+
+2.1 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 in [RFC-2119].
+
+3. STARTTLS Extension
+
+   The STARTTLS extension to SMTP is laid out as follows:
+
+   (1) the name of the SMTP service defined here is STARTTLS;
+
+   (2) the EHLO keyword value associated with the extension is STARTTLS;
+
+   (3) the STARTTLS keyword has no parameters;
+
+   (4) a new SMTP verb, "STARTTLS", is defined;
+
+   (5) no additional parameters are added to any SMTP command.
+
+4. The STARTTLS Keyword
+
+   The STARTTLS keyword is used to tell the SMTP client that the SMTP
+   server allows use of TLS. It takes no parameters.
+
+5. The STARTTLS Command
+
+   The format for the STARTTLS command is:
+
+   STARTTLS
+
+   with no parameters.
+
+   After the client gives the STARTTLS command, the server responds with
+   one of the following reply codes:
+
+   220 Ready to start TLS
+   501 Syntax error (no parameters allowed)
+   454 TLS not available due to temporary reason
+
+   A publicly-referenced SMTP server MUST NOT require use of the
+   STARTTLS extension in order to deliver mail locally. This rule
+   prevents the STARTTLS extension from damaging the interoperability of
+   the Internet's SMTP infrastructure. A publicly-referenced SMTP server
+   is an SMTP server which runs on port 25 of an Internet host listed in
+   the MX record (or A record if an MX record is not present) for the
+   domain name on the right hand side of an Internet mail address.
+
+
+
+
+Hoffman                     Standards Track                     [Page 2]
+
+RFC 2487                 SMTP Service Extension             January 1999
+
+
+   Any SMTP server may refuse to accept messages for relay based on
+   authentication supplied during the TLS negotiation. An SMTP server
+   that is not publicly referenced may refuse to accept any messages for
+   relay or local delivery based on authentication supplied during the
+   TLS negotiation.
+
+   A SMTP server that is not publicly referenced may choose to require
+   that the client perform a TLS negotiation before accepting any
+   commands. In this case, the server SHOULD return the reply code:
+
+   530 Must issue a STARTTLS command first
+
+   to every command other than NOOP, EHLO, STARTTLS, or QUIT. If the
+   client and server are using the ENHANCEDSTATUSCODES ESMTP extension
+   [RFC-2034], the status code to be returned SHOULD be 5.7.0.
+
+   After receiving a 220 response to a STARTTLS command, the client
+   SHOULD start the TLS negotiation before giving any other SMTP
+   commands.
+
+   If the SMTP client is using pipelining as defined in RFC 1854, the
+   STARTTLS command must be the last command in a group.
+
+5.1 Processing After the STARTTLS Command
+
+   After the TLS handshake has been completed, both parties MUST
+   immediately decide whether or not to continue based on the
+   authentication and privacy achieved. The SMTP client and server may
+   decide to move ahead even if the TLS negotiation ended with no
+   authentication and/or no privacy because most SMTP services are
+   performed with no authentication and no privacy, but some SMTP
+   clients or servers may want to continue only if a particular level of
+   authentication and/or privacy was achieved.
+
+   If the SMTP client decides that the level of authentication or
+   privacy is not high enough for it to continue, it SHOULD issue an
+   SMTP QUIT command immediately after the TLS negotiation is complete.
+   If the SMTP server decides that the level of authentication or
+   privacy is not high enough for it to continue, it SHOULD reply to
+   every SMTP command from the client (other than a QUIT command) with
+   the 554 reply code (with a possible text string such as "Command
+   refused due to lack of security").
+
+   The decision of whether or not to believe the authenticity of the
+   other party in a TLS negotiation is a local matter. However, some
+   general rules for the decisions are:
+
+
+
+
+
+Hoffman                     Standards Track                     [Page 3]
+
+RFC 2487                 SMTP Service Extension             January 1999
+
+
+    - A SMTP client would probably only want to authenticate an SMTP
+      server whose server certificate has a domain name that is the
+      domain name that the client thought it was connecting to.
+    - A publicly-referenced  SMTP server would probably want to accept
+      any certificate from an SMTP client, and would possibly want to
+      put distinguishing information about the certificate in the
+      Received header of messages that were relayed or submitted from
+      the client.
+
+5.2 Result of the STARTTLS Command
+
+   Upon completion of the TLS handshake, 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 argument to the EHLO command,
+   which was not obtained from the TLS negotiation itself. The client
+   MUST discard any knowledge obtained from the server, such as the list
+   of SMTP service extensions, which was not obtained from the TLS
+   negotiation itself. The client SHOULD send an EHLO command as the
+   first command after a successful TLS negotiation.
+
+   The list of SMTP service extensions returned in response to an EHLO
+   command received after the TLS handshake MAY be different than the
+   list returned before the TLS handshake. For example, an SMTP server
+   might not want to advertise support for a particular SASL mechanism
+   [SASL] unless a client has sent an appropriate client certificate
+   during a TLS handshake.
+
+   Both the client and the server MUST know if there is a TLS session
+   active.  A client MUST NOT attempt to start a TLS session if a TLS
+   session is already active. A server MUST NOT return the TLS extension
+   in response to an EHLO command received after a TLS handshake has
+   completed.
+
+6. Usage Example
+
+   The following dialog illustrates how a client and server can start a
+   TLS session:
+
+   S: <waits for connection on TCP port 25>
+   C: <opens connection>
+   S: 220 mail.imc.org SMTP service ready
+   C: EHLO mail.ietf.org
+   S: 250-mail.imc.org offers a warm hug of welcome
+   S: 250 STARTTLS
+   C: STARTTLS
+   S: 220 Go ahead
+   C: <starts TLS negotiation>
+
+
+
+Hoffman                     Standards Track                     [Page 4]
+
+RFC 2487                 SMTP Service Extension             January 1999
+
+
+   C & S: <negotiate a TLS session>
+   C & S: <check result of negotiation>
+   C: <continues by sending an SMTP command>
+   . . .
+
+7. Security Considerations
+
+   It should be noted that SMTP is not an end-to-end mechanism. Thus, if
+   an SMTP client/server pair decide to add TLS privacy, they are not
+   securing the transport from the originating mail user agent to the
+   recipient.  Further, because delivery of a single piece of mail may
+   go between more than two SMTP servers, adding TLS privacy to one pair
+   of servers does not mean that the entire SMTP chain has been made
+   private. Further, just because an SMTP server can authenticate an
+   SMTP client, it does not mean that the mail from the SMTP client was
+   authenticated by the SMTP client when the client received it.
+
+   Both the STMP client and server must check the result of the TLS
+   negotiation to see whether acceptable authentication or privacy was
+   achieved. Ignoring this step completely invalidates using TLS for
+   security.  The decision about whether acceptable authentication or
+   privacy was achieved is made locally, is implementation-dependant,
+   and is beyond the scope of this document.
+
+   The SMTP client and server should note carefully the result of the
+   TLS negotiation. If the negotiation results in no privacy, or if it
+   results in privacy using algorithms or key lengths that are deemed
+   not strong enough, or if the authentication is not good enough for
+   either party, the client may choose to end the SMTP session with an
+   immediate QUIT command, or the server may choose to not accept any
+   more SMTP commands.
+
+   A server announcing in an EHLO response that it uses a particular TLS
+   protocol should not pose any security issues, since any use of TLS
+   will be at least as secure as no use of TLS.
+
+   A man-in-the-middle attack can be launched by deleting the "250
+   STARTTLS" response from the server. This would cause the client not
+   to try to start a TLS session. An SMTP client can protect against
+   this attack by recording the fact that a particular SMTP server
+   offers TLS during one session and generating an alarm if it does not
+   appear in the EHLO response for a later session. The lack of TLS
+   during a session SHOULD NOT result in the bouncing of email, although
+   it could result in delayed processing.
+
+
+
+
+
+
+
+Hoffman                     Standards Track                     [Page 5]
+
+RFC 2487                 SMTP Service Extension             January 1999
+
+
+   Before the TLS handshake 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 TLS handshake upon completion of the TLS
+   handshake.
+
+   The STARTTLS extension is not suitable for authenticating the author
+   of an email message unless every hop in the delivery chain, including
+   the submission to the first SMTP server, is authenticated. Another
+   proposal [SMTP-AUTH] can be used to authenticate delivery and MIME
+   security multiparts [MIME-SEC] can be used to authenticate the author
+   of an email message. In addition, the [SMTP-AUTH] proposal offers
+   simpler and more flexible options to authenticate an SMTP client and
+   the SASL EXTERNAL mechanism [SASL] MAY be used in conjunction with
+   the STARTTLS command to provide an authorization identity.
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+Hoffman                     Standards Track                     [Page 6]
+
+RFC 2487                 SMTP Service Extension             January 1999
+
+
+A. References
+
+   [RFC-821]   Postel, J., "Simple Mail Transfer Protocol", RFC 821,
+               August 1982.
+
+   [RFC-1869]  Klensin, J., Freed, N, Rose, M, Stefferud, E. and D.
+               Crocker, "SMTP Service Extensions", STD 10, RFC 1869,
+               November 1995.
+
+   [RFC-2034]  Freed, N., "SMTP Service Extension for Returning Enhanced
+               Error Codes", RFC 2034, October 1996.
+
+   [RFC-2119]  Bradner, S., "Key words for use in RFCs to Indicate
+               Requirement Levels", BCP 14, RFC 2119, March 1997.
+
+   [SASL]      Myers, J., "Simple Authentication and Security Layer
+               (SASL)", RFC 2222, October 1997.
+
+   [SMTP-AUTH] "SMTP Service Extension for Authentication", Work in
+               Progress.
+
+   [TLS]       Dierks, T. and C. Allen, "The TLS Protocol Version 1.0",
+               RFC 2246, January 1999.
+
+B. Author's Address
+
+   Paul Hoffman
+   Internet Mail Consortium
+   127 Segre Place
+   Santa Cruz, CA  95060
+
+   Phone: (831) 426-9827
+   EMail: phoffman@imc.org
+
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+Hoffman                     Standards Track                     [Page 7]
+
+RFC 2487                 SMTP Service Extension             January 1999
+
+
+C.  Full Copyright Statement
+
+   Copyright (C) The Internet Society (1999).  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.
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+Hoffman                     Standards Track                     [Page 8]
+