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SMTP Require TLS Option

The information below is for an old version of the document.
Document Type This is an older version of an Internet-Draft whose latest revision is Replaced
Author Jim Fenton
Last updated 2016-01-10
Replaced by draft-ietf-uta-smtp-require-tls, RFC 8689
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Internet Engineering Task Force                                J. Fenton
Internet-Draft                                          January 10, 2016
Intended status: Experimental
Expires: July 13, 2016

                        SMTP Require TLS Option


   The SMTP STARTTLS option, used in negotiating transport-level
   encryption of SMTP connections, is not as useful from a security
   standpoint as it might be because of its opportunistic nature;
   message delivery is prioritized over security.  This document
   describes a complementary option, REQUIRETLS, which causes message
   delivery to fail if a TLS connection with the required security
   characteristics cannot be negotiated with the next hop MTA or if that
   MTA does not also support REQUIRETLS.  Message originators may
   therefore expect transport security for messages sent with this

Status of This Memo

   This Internet-Draft is submitted in full conformance with the
   provisions of BCP 78 and BCP 79.

   Internet-Drafts are working documents of the Internet Engineering
   Task Force (IETF).  Note that other groups may also distribute
   working documents as Internet-Drafts.  The list of current Internet-
   Drafts is at

   Internet-Drafts are draft documents valid for a maximum of six months
   and may be updated, replaced, or obsoleted by other documents at any
   time.  It is inappropriate to use Internet-Drafts as reference
   material or to cite them other than as "work in progress."

   This Internet-Draft will expire on July 13, 2016.

Copyright Notice

   Copyright (c) 2016 IETF Trust and the persons identified as the
   document authors.  All rights reserved.

   This document is subject to BCP 78 and the IETF Trust's Legal
   Provisions Relating to IETF Documents
   ( in effect on the date of
   publication of this document.  Please review these documents

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   carefully, as they describe your rights and restrictions with respect
   to this document.  Code Components extracted from this document must
   include Simplified BSD License text as described in Section 4.e of
   the Trust Legal Provisions and are provided without warranty as
   described in the Simplified BSD License.

Table of Contents

   1.  Introduction  . . . . . . . . . . . . . . . . . . . . . . . .   2
     1.1.  Requirements Language . . . . . . . . . . . . . . . . . .   3
   2.  The REQUIRETLS Service Extension  . . . . . . . . . . . . . .   3
   3.  REQUIRETLS Semantics  . . . . . . . . . . . . . . . . . . . .   4
     3.1.  REQUIRETLS Receipt Requirements . . . . . . . . . . . . .   4
     3.2.  REQUIRETLS Sender Requirements  . . . . . . . . . . . . .   4
     3.3.  REQUIRETLS Submission . . . . . . . . . . . . . . . . . .   4
     3.4.  Delivery of REQUIRETLS messages . . . . . . . . . . . . .   5
   4.  Error handling  . . . . . . . . . . . . . . . . . . . . . . .   5
   5.  IANA Considerations . . . . . . . . . . . . . . . . . . . . .   5
   6.  Security Considerations . . . . . . . . . . . . . . . . . . .   5
   7.  References  . . . . . . . . . . . . . . . . . . . . . . . . .   6
     7.1.  Normative References  . . . . . . . . . . . . . . . . . .   6
     7.2.  Informative References  . . . . . . . . . . . . . . . . .   7
   Author's Address  . . . . . . . . . . . . . . . . . . . . . . . .   7

1.  Introduction

   The SMTP [RFC5321] STARTTLS service extension [RFC3207] provides a
   means by which an SMTP server and client can negotiate a Transport
   Layer Security (TLS) protected session for the transmission of email
   messages.  In this application, TLS is used only upon mutual
   agreement (successful negotiation) between the client and server; if
   this is not possible, the message is sent unencrypted.  Furthermore,
   even if a TLS protected session is negotiated, it is uncommon for the
   client to abort the SMTP session if certificate validation fails.

   The opportunistic nature of SMTP TLS enables several "on the wire"
   attacks on SMTP security between MTAs.  These include passive
   eavesdropping on connections for which TLS was not negotiated,
   interference in the SMTP protocol to prevent TLS from being
   negotiated (usually followed by subsequent eavesdropping), and
   insertion of a man-in-the-middle attacker taking advantage of the
   lack of server authentication by the client.  Attacks are more
   described in more detail in the Security Considerations section of
   this document.

   The REQUIRETLS SMTP service extension allows the SMTP client to
   specify that all messages sent during a particular session MUST be
   sent over a TLS protected session with specified security

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   characteristics.  It also requires that the SMTP server advertise
   that it also supports REQUIRETLS, in effect promising that it will
   honor the requirement to negotiate STARTTLS and REQUIRETLS for all
   onward transmissions of any of the messages contained in this

1.1.  Requirements Language

   The key words "MUST", "MUST NOT", "REQUIRED", "SHALL", "SHALL NOT",
   document are to be interpreted as described in RFC 2119 [RFC2119].

2.  The REQUIRETLS Service Extension

   1.  The textual name of the extension is "Require TLS".

   2.  The EHLO keyword value associated with this extension is

   3.  One additional SMTP verb, also named REQUIRETLS, is defined by
       this extension.

   4.  Two new SMTP status codes are defined by this extension to convey
       error conditions resulting from failure of the client to
       negotiate a TLS connection with the required security and as a
       result of an attempt to send to a server not also supporting the
       REQUIRETLS extension.

   An optional parameter to the REQUIRETLS SMTP verb, if present,
   specifies the method(s) for server authentication that the server
   MUST use for any onward transmission of the following messages.  The
   parameter takes the form of either a single value or comma-separated
   list, separated from the verb by a single "=" (equals-sign)
   character.  If present, the parameter MUST take one or more of the
   following values:

   o  CHAIN - The certificate presented by the SMTP server MUST verify
      successfully in a trust chain leading to a certificate trusted by
      the SMTP client.  The choice of trusted (root) certificates by the
      client is at their own discretion.  The client MAY choose to use
      the certificate set maintained by the CA/B forum [citation needed]
      for this purpose.

   o  DANE - The certificate presented by the SMTP server MUST verify
      succesfully using DANE as specified in RFC 7672 [RFC7672].

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   If the parameter is not present, the default behavior is that the
   certificate presented by the SMTP server MAY be authenticated, but is
   not required to be.

3.  REQUIRETLS Semantics

3.1.  REQUIRETLS Receipt Requirements

   Upon receipt of a REQUIRETLS verb from a client, an SMTP server MUST
   tag all subsequent messages received during that session as requiring
   TLS transmission with the specified authentication method(s).  The
   manner in which this tagging takes place is implementation-dependent.

3.2.  REQUIRETLS Sender Requirements

   When sending a message tagged with a TLS requirement, the sending
   (client) MTA MUST:

   o  Open an SMTP session with the peer SMTP server using the EHLO
      verb.  If the server does not advertise the REQUIRETLS capability,
      the client MUST bounce the message with a TBD error code as
      described in section xxx.

   o  Negotiate a TLS-protected SMTP session with its peer SMTP server
      and authenticate the server's certificate with the specified
      authentication method.  If it is unable to do so, the client MUST
      bounce the message with a TBD error code as described in section

   o  Issue the REQUIRETLS verb with the required authentication
      method(s), if any.

   o  Transmit the associated message(s).

   o  If multiple messages are to be transmitted with different
      authentication requirements, the REQUIRETLS command can be
      repeated to change the authentication method for subsequent
      messages.  However, the TLS connection being used MUST satisfy the
      new as well as the former authentication method(s).

3.3.  REQUIRETLS Submission

   An MUA or other agent making the initial introduction of a message to
   SMTP has authority to decide whether to require TLS, and if so, using
   what authentication method(s).  It does so by issuing the REQUIRETLS
   verb in the SMTP session associated with message submission.  This
   MAY be done based on a user interface selection, on a header field
   included in the message, or based on policy.  The manner in which the

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   decision to require TLS is made is implementation-dependent and is
   beyond the scope of this specification.

3.4.  Delivery of REQUIRETLS messages

   Messages are usually delivered to end users using protocols other
   than SMTP such as IMAP [RFC3501], POP [RFC1939], or web mail systems.
   Mail delivery agents supporting REQUIRETLS SHOULD require that
   message delivery take place over authenticated, encrypted channels.

4.  Error handling

   Error ("bounce") messages contain important metadata, and therefore
   MUST be protected in the same manner as the original message.  All
   error handling, whether resulting from a REQUIRETLS error or some
   other, MUST employ REQUIRETLS at the same authentication method(s) as
   the message that caused the error to occur.

   It should be noted that the path from the origination of an error
   bounce message back to the MAIL FROM address may not share the same
   REQUIRETLS support as the forward path.  Therefore, users of
   REQUIRETLS are advised to make sure that they are capable of
   receiving mail using REQUIRETLS at the same authentication method(s)
   as messages they send.  Otherwise, such error bounces will be lost.

5.  IANA Considerations

   If published as an RFC, this draft requests the addition of the
   keyword REQUIRETLS to the SMTP Service Extensions registry MAILPARAMS

   If published as an RFC, this draft also requests the creation of a
   registry, REQUIRETLS Security Requirements, to be initially populated
   with the CHAIN and DANE keywords.

   This section is to be removed during conversion into an RFC by the
   RFC Editor.

6.  Security Considerations

   The purpose of REQUIRETLS is to improve communications security for
   email by giving the originator of a message an expectation that it
   will be transmitted in an encrypted form "over the wire".  When used,
   REQUIRETLS changes the traditional behavior of email transmission,
   which favors delivery over the ability to send email messages using
   transport-layer security, to one in which messages are not
   transmitted unless the required security is available.

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   REQUIRETLS is negotiated over SMTP by the MTAs along the message
   transmission path.  Accordingly, a bad-actor MTA could misrepresent
   its support of REQUIRETLS and/or actively strip REQUIRETLS tags from
   messages it handles.  However, since the originator of a message
   trusts the MTA that it submits the message to forward the message
   according to its instructions, and the recipient trusts MTAs that it
   lists in its MX records.  MTAs that can be trusted with the cleartext
   of messages (since encryption is at the transport layer) are assumed
   to also be trustworthy to honor their REQUIRETLS obligations as well.

   One exception to this trust can occur if an attacker is able to spoof
   the MX record(s) for the receiving domain to an earlier hop MTA.  The
   attacker could then successfully negotiate TLS with the earlier MTA,
   since it should be able to obtain a certificate for the hostname it
   spoofed.  This is actually a more generic attack on SMTP TLS that is
   also effective against REQUIRETLS since the attacker could forward
   the message onward without REQUIRETLS.  For these reasons, domains
   receiving email SHOULD deploy DNSSEC [RFC4033].

   It should be reemphasized that since SMTP TLS is a transport-layer
   security protocol, messages sent using REQUIRETLS are not encrypted
   end-to-end and are visible to MTAs that are part of the message
   delivery path.  Messages containing sensitive information that MTAs
   should not have access to MUST be sent using end-to-end content
   encryption such as OpenPGP [RFC4880] or S/MIME [RFC5751].

7.  References

7.1.  Normative References

              Internet Assigned Numbers Authority (IANA), "IANA Mail
              Parameters", 2007,

   [RFC2119]  Bradner, S., "Key words for use in RFCs to Indicate
              Requirement Levels", BCP 14, RFC 2119,
              DOI 10.17487/RFC2119, March 1997,

   [RFC3207]  Hoffman, P., "SMTP Service Extension for Secure SMTP over
              Transport Layer Security", RFC 3207, DOI 10.17487/RFC3207,
              February 2002, <>.

   [RFC5321]  Klensin, J., "Simple Mail Transfer Protocol", RFC 5321,
              DOI 10.17487/RFC5321, October 2008,

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7.2.  Informative References

   [RFC1939]  Myers, J. and M. Rose, "Post Office Protocol - Version 3",
              STD 53, RFC 1939, DOI 10.17487/RFC1939, May 1996,

              4rev1", RFC 3501, DOI 10.17487/RFC3501, March 2003,

   [RFC4033]  Arends, R., Austein, R., Larson, M., Massey, D., and S.
              Rose, "DNS Security Introduction and Requirements",
              RFC 4033, DOI 10.17487/RFC4033, March 2005,

   [RFC4880]  Callas, J., Donnerhacke, L., Finney, H., Shaw, D., and R.
              Thayer, "OpenPGP Message Format", RFC 4880,
              DOI 10.17487/RFC4880, November 2007,

   [RFC5751]  Ramsdell, B. and S. Turner, "Secure/Multipurpose Internet
              Mail Extensions (S/MIME) Version 3.2 Message
              Specification", RFC 5751, DOI 10.17487/RFC5751, January
              2010, <>.

   [RFC7672]  Dukhovni, V. and W. Hardaker, "SMTP Security via
              Opportunistic DNS-Based Authentication of Named Entities
              (DANE) Transport Layer Security (TLS)", RFC 7672,
              DOI 10.17487/RFC7672, October 2015,

Author's Address

   Jim Fenton
   704 Benvenue Avenue
   Los Altos, California  94024


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