Internet DRAFT - draft-wchuang-msmd

draft-wchuang-msmd







Application Area Working Group                                 W. Chuang
Internet-Draft                                            N. Lidzborkski
Expires: April 18, 2014                                     E. Bursztein
                                                            Google, Inc.
                                                        October 15, 2013


                  MSMD: Mandatory Secure Mail Delivery
                         draft-wchuang-msmd-00

Abstract

   Opportunistic SMTP TLS does not enforce electronic mail delivery
   using TLS leading to potential loss of privacy and security.  We
   propose an optional mail header extension "mandatory-secure-mail-
   delivery:" and SMTP EHLO response extension "MSMD" that indicates
   mail must be delivered privately using TLS and with integrity using
   DKIM, and thereby provide a security guarantee to the user.  When
   mail is sent with the header indicating privacy and integrity and if
   the receiving party does not support this, the mail is instead
   bounced.  To protect the mail after delivery, the destination SMTP
   server must advertise its capabilities as part of the EHLO response,
   and the sender can choose whether the destination is able to honor
   the privacy requirements specified on the mail header.

Status of This Memo

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   This Internet-Draft will expire on April 18, 2014.

Copyright Notice

   Copyright (c) 2013 IETF Trust and the persons identified as the
   document authors.  All rights reserved.





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   This document is subject to BCP 78 and the IETF Trust's Legal
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Table of Contents

   1.  Introduction  . . . . . . . . . . . . . . . . . . . . . . . .   2
   2.  Mandatory Private Delivery Specification  . . . . . . . . . .   5
     2.1.  MSMD Mail Header  . . . . . . . . . . . . . . . . . . . .   5
     2.2.  MSMD SMTP Extension . . . . . . . . . . . . . . . . . . .   6
     2.3.  Domain Keys Identified Mail . . . . . . . . . . . . . . .   6
     2.4.  Deployment Concerns . . . . . . . . . . . . . . . . . . .   6
     2.5.  Delivery Failure Notification . . . . . . . . . . . . . .   7
     2.6.  Mail User Agent Support . . . . . . . . . . . . . . . . .   7
       2.6.1.  IMAP Extension  . . . . . . . . . . . . . . . . . . .   8
       2.6.2.  POP3 Extension  . . . . . . . . . . . . . . . . . . .   8
     2.7.  Compatibility . . . . . . . . . . . . . . . . . . . . . .   8
   3.  TLS . . . . . . . . . . . . . . . . . . . . . . . . . . . . .   8
   4.  Optional Requirements and Capabilities  . . . . . . . . . . .  11
     4.1.  Mail Header Requirements  . . . . . . . . . . . . . . . .  11
     4.2.  SMTP MSMD Capabilities  . . . . . . . . . . . . . . . . .  12
     4.3.  Example with Requirements and Capabilities  . . . . . . .  12
   5.  Recommendations . . . . . . . . . . . . . . . . . . . . . . .  13
   6.  Security Considerations . . . . . . . . . . . . . . . . . . .  14
   7.  Acknowledgements  . . . . . . . . . . . . . . . . . . . . . .  14
   8.  References  . . . . . . . . . . . . . . . . . . . . . . . . .  14
   Authors' Addresses  . . . . . . . . . . . . . . . . . . . . . . .  15

1.  Introduction

   Opportunistic SMTP TLS [RFC3207] does not enforce electronic mail
   delivery using TLS.  This means that even if a user wishing to send
   mail has a provider that supports SMTP TLS, the provider does not
   necessarily deliver mail over TLS depending on whether the peer
   supports TLS or if the TLS negotiation fails.  Unfortunately our
   observation is that most mail providers do not support SMTP TLS.
   These deployment problems are made worse because users typically do
   not have control over delivery and do not know whether their message
   will be delivered securely.  Also users have an assumption that their



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   mail content will be delivered without modifications though in fact
   with traditional SMTP [RFC5321] there is no assurance of this.  This
   combination diminishes trust amongst electronic mail users.

   We believe that finding a solution will become more important as
   recent news indicates that eavesdroppers will increasingly targeting
   electronic mail delivery as a likely point of attack (if not
   already).  This is motivated by the observation that web client side
   security has steadily improved due to increasingly effective and
   deployed encryption [1] while most mail delivery remains unencrypted.
   Moreover SMTP TLS is more susceptible to active attack such as Man-
   in-the-Middle (MitM) than web client security.  Attacks such as
   certificate forgery or TLS downgrade have been mitigated with
   certificate pinning [2] and HSTS [RFC6797].  No such mechanism exists
   today with SMTP TLS.

   The main alternative is to use encrypted mail such as PGP/MIME and S/
   MIME which keep the mail body private during delivery.  However they
   do nothing to guarantee private mail delivery, and traditional SMTP
   transmits the sender and the recipient in the clear.  Thus even PGP/
   MIME [RFC3156] or S/MIME [RFC5751] encrypted mail is susceptible to
   meta-data surveillance.

   We propose optional mail extensions that indicates that mail delivery
   must be delivered privately using TLS, and must be signed with DKIM
   to indicate authenticity and integrity.  The user or their provider
   can choose to set a new mail header "mandatory-secure-mail-delivery:"
   that indicates private mail distribution as described in Section 2.1.
   When mail is sent with this header, the SMTP client (sending SMTP
   server) checks if the receiving side supports encrypted and signed
   private delivery.  If not, the mail is bounced.  The bounce message
   must be returned to sender securely as well, otherwise the message
   must be dropped.  A courtesy message may be sent to the recipient
   depending on the sender's settings.  Another concern is maintaining
   the security of the mail at the destination and beyond.  The SMTP
   server (destination SMTP server) must advertise it supports and
   enforces this protocol as part of the EHLO response using the
   extension "MSMD" which the sender will verify as described in
   Section 2.2.  Mail providers that honor this protocol should ensure
   that derivative mails created such as when forwarding and replying
   maintain the requested private mail delivery property by copying the
   security header to the new message.  This is not mandatory in the
   base protocol because honoring it would impose restrictions for all
   Mail User Agent interfaces that would be a substantial barrier to
   entry.  In the following sections, we show how we can elevate the
   "should" to "must" for securing derivative mails.  Thus with the base
   protocol at minimum a sender can be certain that a sent mail will be
   delivered privately and unaltered.



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   The protocol can impose additional security requirement options via
   arguments on the message-header as described in Section 4.1 that the
   SMTP client can verify.  As part of this verification process, the
   SMTP server can also advertise domain security capability options as
   part of the EHLO response as described in Section 4.2.  They can help
   insure the recipient's mail provider is just as capable of verifying
   the security requirements as the sender's provider.  Options enable
   the protocol to flexibly extend the definition of security to meet
   different needs, and to evolve as the security standing of the
   ecosystem improves.

   Options are particularly useful if the sender wishes to mandate
   enforcement of the protocol for the entire conversation meaning
   through all derived forwarded and replied mails.  We propose a Secure
   Conversation and Access (SCA) option that mandates for all mail
   messages so marked, all derived mail must also be so marked.  Any
   mail agent in the domain must honor and propagate the additional SCA
   protocol in addition to the base protocol.  This imposes a powerful
   and stringent requirement over all MUA such as IMAP or POP3 to
   support the protocol as described in Section 2.6, or not be able to
   access these messages.  SCA also requires that these clients must
   access these messages privately over an encrypted channel.  Thus a
   sender can be sure that a sent mail and its derivatives will be sent
   and accessed securely.

   Via options we can also specify TLS settings to improve security.  Of
   the threats to TLS, perhaps the most difficult to protect against is
   MitM since the adversary impersonates the endpoint.  To defend
   against this, we bundle various TLS settings into tiers corresponding
   to the capabilities of ecosystem that improves the ability to reject
   MitM peers.

   This example illustrates the message declaration, and that of the
   recipient i.e. the base protocol.  It also illustrates the
   verification by the sender.  We use the convention "C:" for client
   and "S:" for server.

      Some mail message has a private delivery request, which specifies the
      mail header:
      mandatory-secure-mail-delivery:

      The SMTP exchange protocol appears as follows:
      S: <waits for connection on TCP port 25>
      C: <opens connection>
      S: 220 mail.server.org SMTP service ready
      C: EHLO mail.client.com
      S: 250-mail.server.org welcomes you
      S: 250-STARTTLS



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      S: 250-MSMD
      S: 250 DSN
      C: STARTTLS
      S: 220 Go ahead
      C: <starts TLS negotiation using default TLS requirements>
      C & S: <negotiate a TLS session>
      C: EHLO mail.client.com
      S: 250-mail.server.org welcomes you
      S: 250-MSMD
      S: 250 DSN
      C: <Perform MSMD Requirements Check: On failure close the connection>
      C: DATA
      C: <Send mail with DKIM signature>

      Note: 1) TLS requirements are passed to the TLS setup 2) after the
      second EHLO, that there is a MSMD Requirements Check. The latter
      verifies that the TLS connection has started, and that the MSMD
      SMTP extension was presented on the second EHLO.

                   Figure 1: Basic MSMD Protocol Example

2.  Mandatory Private Delivery Specification

2.1.  MSMD Mail Header

   We propose a new optional mail header: [RFC5322] "mandatory-secure-
   mail-delivery:" (MSMD) in accordance with [RFC3864].  The MSMD header
   indicates that this message must be privately distributed using
   encryption.  It may have associated with it parameters that impose
   additional requirements on the delivery security and destination
   security.  The parameters will be discussed further in Section 4.1.
   Requirements may only be applied if the user's mail provider can
   support those requirements.

   Mail messages derived from a mail message with the MSMD message
   header should copy this header along with any options, and those
   derived messages must honor the security protocol.  Examples of
   deriving the message are replying and forwarding the mail message.
   If the Secure Conversation and Access option is specified, the
   derived message must copy the message header.  The user is free to
   download the content, or distribute the contents via GUI means such
   as cut or copy and paste without the header.  The distinction is
   meant to protect mail content against accidental exposure via
   unencrypted mail delivery, but not stymie legitimate every day use of
   mail content.  Derived mail may add additional security requirements
   to the MSMD message header but must not remove any requirements.





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2.2.  MSMD SMTP Extension

   When delivering the mail message, the SMTP client must verify that
   the destination will honor maintaining the MSMD protocol once the
   message is delivered.  To support this, the SMTP server advertises
   that it supports the protocol via a MSMD SMTP extension [RFC5321].
   This means that during the EHLO response, there will be a "MSMD"
   keyword, and that it may be followed by parameters describing
   additional capabilities of the server.  The capabilities are
   described in Section 4.2.  The SMTP client verifies that the SMTP
   server has both MSMD and STARTTLS extensions, then establishes the
   TLS connection.  As the connection at this point is encrypted and
   private, it redoes the EHLO, gathering any capabilities specified by
   the server.  Then it does the MSMD requirements check using the
   securely communicated capabilities values.  In the basic
   configuration meaning without any additional requirements or
   capabilities, SMTP client just verifies the connection is in TLS, and
   re-verifies that there is a MSMD SMTP extension.  Success allows mail
   delivery to continue, while failure causes a notification to be sent
   as described Section 2.5 and the TLS and SMTP connection is closed
   and reset.  Any other Mail Transfer Agent must support this protocol
   in a similar fashion or be prevent from transferring mails marked by
   the MSMD header.

2.3.  Domain Keys Identified Mail

   All MSMD market mails must be sent with DKIM [RFC6376] signatures to
   provide assurance for the integrity and authenticity of the mail
   message.  Similarly MSMD SMTP Servers must verify received DKIM
   messages.  In the MSMD context, how DKIM handles failed signature
   verification is up to the mail provider.  MSMD mandates that at least
   the message body and "mandatory-secure-mail-delivery:" header be
   signed leaving the rest as implementation dependent.

2.4.  Deployment Concerns

   Though much of this proposal is concerned with security of SMTP mail
   delivery, the base protocol recommends that all other means of
   accessing the protected mail via Mail User Agents should be similarly
   protected.  This means all mail fetch mechanism should similarly
   honor the encrypted delivery requirement and should propagate the
   MSMD header to derived mails.

   If the Secure Conversation and Access option is given, the
   restrictions on MUA become mandatory.  Also to prevent eavesdropping
   during fetch, SCA places a further requirement to encrypt access.  If
   the MUA cannot insure propagating the MSMD protocol or provide
   private access, that they must be prevented from accessing user data



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   marked with the MSMD security header.  Upon access failure these
   clients should use whatever error reporting mechanism built into the
   protocol to provide a notification indicating the cause and an
   alternative means of accessing the mail securely.

   Mailing list forwarders supporting the MSMD protocol must also check
   if each list recipient honors the protocol in the same way as a
   single recipient.  Failure to meet the security requirements results
   in the message not being delivered and may result in notification of
   delivery failure.  These forwarders must also insure that DKIM
   verification will succeed either by maintaining the exact same MSMD
   header and message body, or by re-generating the DKIM signature.

2.5.  Delivery Failure Notification

   For message delivery failure due to insufficient security, the sender
   will be notified via a non-delivery notification message [RFC3461].
   For diagnostics, these security bounce messages should include at
   least a description of the failure including which step of the SMTP
   handshake that failed, any missing requested options, and identifying
   information such as destination and subject.  Security bounce
   messages must be delivered with the same security guarantees as the
   originating message.  This means that the MSMD header is copied to
   the bounce message, and honored as with the original, and a DKIM
   signature placed on the message.  To prevent an endless notification
   loop, delivery failure of these security bounce messages due to MSMD
   protocol failure causes the message to be silently dropped.

   Upon security failure on delivery, the SMTP client may still sent a
   courtesy message to the recipient depending on the header options, to
   let them know that mail is missing due to security failure at
   delivery time.  The courtesy message is optional in case the sender
   insists on keeping private all meta-data that might be leaked by
   courtesy messages.  It differs from security bounce messages in that
   the security header is not propagated, and the information passed is
   more restricted.  The courtesy message should just provide enough to
   identify the message and cause but no more i.e. identifying
   information such as from: and subject: but not the body or any
   additional user identifying header information.

2.6.  Mail User Agent Support

   Assuming that the Secure Conversation Mail option applies to the mail
   message, Mail User Agents such as IMAP or POP3 Clients must honor the
   MSMD security protocol, and clients must be able to prove to the
   servers they are capable of honoring the protocol.  Such MUA servers
   must be able to display the MSMD extension, and the MUA clients must
   be able present to the server its ability to honor the MSMD protocol.



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   If MUA clients does not display support for MSMD, then MSMD MUA
   servers must prevent access to MSMD marked and protected mail.

2.6.1.  IMAP Extension

   In the case of IMAP [RFC3501], it provides a CAPABILITY command to
   describe the server extensions.  We propose a new MSMD capability to
   IMAP where "MSMD" appears in the CAPABILITY response, and a new
   "MSMD" command that announces to the server that the client supports
   the MSMD protocol.

2.6.2.  POP3 Extension

   Like IMAP, POP3 [RFC1939], it provides a CAPA [RFC2449] command to
   describe the server extensions.  We propose a new MSMD capability
   where "MSMD" appears in the CAPA response, and a new "MSMD" command
   so that the client can indicate to the server it supports the MSMD
   protocol.

2.7.  Compatibility

   Specification of the MSMD security header is on a per message basis.
   This allows the sender to fallback to clear-text delivery for
   backwards compatibility for recipients that don't support the
   protocol and don't need the security it mandates.  In the expected
   case, when the sender starts composing the mail, they can check the
   GUI to see if the recipient can support MSMD, and if not then elect
   to send mail insecurely or not at all.  That said, we expect that
   over time as the ecosystem will upgrade its security capability
   meaning that MSMD support becomes the norm.  Once that happens, it is
   easy to imagine that a mail provider would make MSMD mandatory.

   The Secure Conversation and Access option also provides a significant
   increase in privacy by mandating restricted access after delivery.
   This poses a policy issue, as the recipient has mandatory restriction
   placed on mail in their inbox that they may not want.  Thus we
   imagine that this option be used only in conversations where privacy
   is required such as by business need, and where all parties would not
   object to the restrictions.  With other conversations the sender
   could use the base MSMD protocol or even clear text delivery.  Also
   these restrictions are caused by infrastructure limitations that
   should improve over time.  Once MSMD and SCA support becomes
   universal then this restriction become moot.

3.  TLS

   TLS can be configured to significantly degrade eavesdropping and
   MitM.  They are organized into tiers corresponding to ability of the



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   ecosystem to support the features, and are meant to evolve and be
   upgraded to draw upon improved techniques for stopping these threats.
   The following list are the current TLS parameters that MSMD controls.

   TLS Version  Describes the TLS version.  Currently this is restricted
      TLS only and version "1.0" (SSL version 3,1) or greater must be
      supported.

   CipherSuite  Describes the TLS cipher as a selector based on the
      values from IANA registry for TLS [RFC5246].  Anonymous Diffie-
      Hellman key exchange and RC4 cipher shall not be allowed.

   Public Key Size  Describes the SMTP client/server minimum TLS
      certificate CA certificate public key size.  MSMD requires that
      key sizes of 1024, 2048, 4096 be supported for RSA, DSA and
      Diffie-Hellman based algorithms, and 250 for Elliptic-Curve
      Cryptography if supported.  It is recommended that larger sizes be
      supported as well.

   Public Key Type  Describes the SMTP server TLS [RFC5246] public key
      type.  MSMD requires that RSA be supported, and others are
      optional.

   Symmetric Key Size  Describes the SMTP server TLS [RFC5246] symmetric
      cipher key size.  Both 128 and 256 bits must be supported.

   Check Server Certificate  This specifies the mechanism by which the
      SMTP TLS server certificate are verified.  Ability to use PKI
      verification of X.509 certificate [RFC5280] using "CA"
      (Certificate Authority) must be supported, though actual
      verification is recommended.  We recommend that certificate naming
      standardize [RFC6125] to setting the DNS-ID from the MX record
      host name.  We also recommend using improved PKI such as
      Certificate Transparency [RFC6962].

   To reiterate, the baseline TLS constraints for all MSMD
   implementation with or without specifying the "tls" requirement
   option is the following:

   o  TLS version >= "1.0"

   o  MSMD Public key exchange must support RSA.

   o  Public key exchange shall not use anonymous Diffie-Hellman.

   o  Cipher shall not use RC4.

   o  RSA/DSA/DH Public Key Size >= 1024 or ECC Public Key Size >= 250



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   o  Symmetric Key Size >= 128

   o  Support for CA PKI verification of X.509 certificate.

   If the "tls" requirement option is specified, then it must specify
   one of two tiers.  The tiers corresponding to what can be deployed
   today (circa 2013) with reasonable support from ecosystem.

   o  Tier 1- Baseline strong TLS.  Assumes TLS baseline.

      *  TLS version >= "1.2"

      *  Public key exchange must use ephemeral Diffie-Hellman for
         perfect forward secrecy.

      *  RSA/DSA/DH Public Key Size >= 2048 or ECC Public Key Size >=
         250

   o  Tier 2- Resist MitM- Assumes capabilities of tier 1.

      *  Check Server Certificate- should check for: path, expiry, and
         trusted CA root.  Self-signed certificates shall not not
         verify.

      *  DNSSEC- DNS name look up must look up and verify security
         extensions.  In other words the "ds" DNSSEC requirement option
         is implicitly set, though it is recommended the "ds"
         requirement should still be explicitly appended for
         readability.

      *  Require that certificate naming standardize [RFC6125] to
         setting the DNS-ID from the MX record host name.

   We anticipate more tiers being defined particularly to improve PKI.

   Certificate naming of identifiers for SMTP servers has been recently
   rigorously defined in [RFC6125].  MSMD recommends (and at Tier 2
   requires) the use of this naming scheme for the certificate
   identifiers.  The certificate DNS-ID identifier contents should be
   the SMTP MX host name, and if there are more than one host name than
   multiple DNS-ID names may be specified.  The certificate common
   identifier CN-ID may also be set but with restrictions as noted in
   [RFC6125].  There are also restrictions for identifier wild-cards
   '*'.  An example of the naming scheme is in Figure 2.

       MX Record for gmail.com:
       gmail.com.      3600    IN  MX  10 alt1.gmail-smtp-in.l.google.com.
       gmail.com.      3600    IN  MX  5 gmail-smtp-in.l.google.com.



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       SMTP X.509 Certificate recommended identifier bindings:
       DNS-ID: gmail-smtp-in.l.google.com
       DNS-ID: alt1.gmail-smtp-in.l.google.com.

                   Figure 2: Certificate Naming for SMTP

4.  Optional Requirements and Capabilities

   To allow for different security requirements and to allow for future
   extension, this protocol supports options.  The MSMD message header
   may take additional arguments that act as requirements during the
   MSMD requirements check.  The requirements specify expressions that
   have values bound to it during the TLS setup and the expression must
   evaluate to true.  Requirements may be interpreted by other mail
   components outside of mail delivery e.g. SCA.  The MSMD SMTP EHLO
   extension provides the means to display additional capabilities that
   the server can provide, and can bind values used for the requirements
   check.  To summarize, options serve the following purposes:

   o  Constraints on TLS

   o  Constraints on recipient- Ensure the recipient mail provider can
      maintain security when the message is forwarded or replied-to from
      that provider.

   o  Settings describing the treatment of the message outside of the
      mail delivery

4.1.  Mail Header Requirements

   To simplify the treatment of MSMD requirements, they are all treated
   as expressions with the following rules for the evaluation.
   Requirement names are variables that may be bound to values from SMTP
   extension capabilities or bound to a default value as specified.
   Three value types are currently allowed: boolean, integer or string.
   They initially are bound to respectively False, 0, or "".  All may
   also be set to "undef" meaning not assigned which is treated as
   False.  Expressions support basic comparisons i.e. "==", "!=", "<",
   ">", "<=", and ">=".  They also support composition with "AND", and
   "OR" and precedence group "()", as well as negation "NOT".  Operator
   order of precedence follows the Python language.  Requirement names
   and operators are case insensitive.  One syntactic sugar is allowed:

   1.  If multiple requirements are presented in a sequence separated
       only by white-space, they are treated as composed with "AND".

   The following list describes requirements that may be placed with
   "mandatory-secure-mail-delivery:" header.  Each requirement has a



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   short name and a longer description name.  The short name should be
   used in the mail header to save transmission resources.

   sca  Secure Conversation and Access- as described in Section 2.4.
      (type: boolean)

   ds DNSSEC- Use DNSSEC for name service look-up.  Look-up must verify
      the signatures of DNS records.  (type: boolean)

   m  Message- After MSMD security check failure, forward to the
      destination a courtesy notice as specified in Section 2.5. (type:
      boolean)

   v  Version- The version value for MSMD.  This starts at 0. (type:
      int)

   tls  TLS Tier- As describes in Section 3 one can specify bundles or
      tiers of TLS settings.  The allowed tiers are 1, and 2. (type:
      int)

4.2.  SMTP MSMD Capabilities

   As part of the EHLO response, additional optional capabilities are
   advertised.  The capabilities names are variables bound effectively
   as key-value pairs.  These results become available in the MSMD
   requirements check evaluation.  Unadorned names are bound to "true",
   however if the name is followed by "=" and a value, then the name is
   bound to that value.  Capabilities are also case insensitive.

   sca  Secure Conversation and Access- SMTP Server supports SCA.

   ds DNSSEC- SMTP Server uses DNSSEC for name service look-up.

   m  Message- MSMD security check failure sends a courtesy notice.

   v  Version- The version number for MSMD.

   tls  TLS Tier- The version number for TLS tiers

4.3.  Example with Requirements and Capabilities

   The following illustrates how the options would be used.  A company
   want mail delivery to their customers that mitigates eavesdropping
   and MitM attacks.  To do so, this company would like to specify the
   use of perfect forward secrecy, DNSSEC, and X.509 CA PKI certificates
   verification during mail delivery.  Currently the latter two
   requirements are not yet deployed for many mail providers, but will
   likely be available in the near future.  So today this company just



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   uses MSMD with baseline TLS encryption settings for mail delivery as
   described in the earlier example in Figure 1.  Later when supported,
   the company specifies those three properties for new mail messages
   using the MSMD requirement option "tls>=2".  This is illustrated in
   the following example in Figure 3

      The mail message requests perfect forward secrecy, DNSSEC, and
      X.509 certificate verification by setting the header to:
      mandatory-secure-mail-delivery: tls>=2 ds

      S: <waits for connection on TCP port 25>
      C: <opens connection>
      S: 220 mail.server.org SMTP service ready
      C: EHLO mail.client.com
      S: 250-mail.server.org welcomes you
      S: 250-STARTTLS
      S: 250-MSMD sca m tls=2 ds
      S: 250 DSN
      C: STARTTLS
      S: 220 Go ahead
      C: <starts TLS negotiation>
      C & S: <negotiate a TLS session w/ECDHE-RSA-AES128-SHA>
      C: EHLO mail.client.com
      S: 250-mail.server.org welcomes you
      S: 250-MSMD sca m tls=2 ds
      S: 250 DSN
      C: <Perform MSMD Requirements Check: On failure close the connection>
      C: DATA
      C: <Send mail with DKIM signature>

      During the MSMD Requirements check the requirements expands as follows:
      tls>=2 AND ds
      2>=2 AND true

      This evaluates true and passes, as does the baseline MSMD
      requirements check.  The passing MSMD requirements check indicates
      the recipient provider can maintain at least the same security as
      requested for this message.

                      Figure 3: MSMD Options Example

5.  Recommendations

   Some recommendations that assist the effectiveness of this protocol:

   o  During composition of the mail message that the user be able to
      control setting of MSMD header and SCA option though not
      necessarily the other options.



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   o  GUI should assist the user in predicting whether delivery will
      succeed when the MSMD feature is selected using provider modeling
      and other means.

6.  Security Considerations

   The ability of the protocol to maintain security of mail content
   depends on the effectiveness of peer mail systems implementation of
   this protocol.  Since enforcement is voluntary and easily subverted
   by bad implementations, we propose a blacklist list of mail providers
   that advertise support but are known to have flawed implementations.
   This list would be maintained and adjudicated by a yet to be decided
   third party.  Implementations should obtain the blacklist, and
   prevent delivery of MSMD messages to these mail providers.

7.  Acknowledgements

   The authors wish to acknowledge the very useful comments and
   suggestions from: Brandon Long, Adam Langley, Danesh Irani, Ian
   Fette, and Robert Chien.

8.  References

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

   [RFC2449]  Gellens, R., Newman, C., and L. Lundblade, "POP3 Extension
              Mechanism", RFC 2449, November 1998.

   [RFC2971]  Showalter, T., "IMAP4 ID extension", RFC 2971, October
              2000.

   [RFC3156]  Elkins, M., Del Torto, D., Levien, R., and T. Roessler,
              "MIME Security with OpenPGP", RFC 3156, August 2001.

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

   [RFC3461]  Moore, K., "Simple Mail Transfer Protocol (SMTP) Service
              Extension for Delivery Status Notifications (DSNs)", RFC
              3461, January 2003.

   [RFC3501]  Crispin, M., "INTERNET MESSAGE ACCESS PROTOCOL - VERSION
              4rev1", RFC 3501, March 2003.

   [RFC3864]  Klyne, G., Nottingham, M., and J. Mogul, "Registration
              Procedures for Message Header Fields", BCP 90, RFC 3864,
              September 2004.



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   [RFC5246]  Dierks, T. and E. Rescorla, "The Transport Layer Security
              (TLS) Protocol Version 1.2", RFC 5246, August 2008.

   [RFC5280]  Cooper, D., Santesson, S., Farrell, S., Boeyen, S.,
              Housley, R., and W. Polk, "Internet X.509 Public Key
              Infrastructure Certificate and Certificate Revocation List
              (CRL) Profile", RFC 5280, May 2008.

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

   [RFC5322]  Resnick, P., Ed., "Internet Message Format", RFC 5322,
              October 2008.

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

   [RFC6125]  Saint-Andre, P. and J. Hodges, "Representation and
              Verification of Domain-Based Application Service Identity
              within Internet Public Key Infrastructure Using X.509
              (PKIX) Certificates in the Context of Transport Layer
              Security (TLS)", RFC 6125, March 2011.

   [RFC6376]  Crocker, D., Hansen, T., and M. Kucherawy, "DomainKeys
              Identified Mail (DKIM) Signatures", STD 76, RFC 6376,
              September 2011.

   [RFC6698]  Hoffman, P. and J. Schlyter, "The DNS-Based Authentication
              of Named Entities (DANE) Transport Layer Security (TLS)
              Protocol: TLSA", RFC 6698, August 2012.

   [RFC6797]  Hodges, J., Jackson, C., and A. Barth, "HTTP Strict
              Transport Security (HSTS)", RFC 6797, November 2012.

   [RFC6962]  Laurie, B., Langley, A., and E. Kasper, "Certificate
              Transparency", RFC 6962, June 2013.

Authors' Addresses

   Weihaw Chuang
   Google, Inc.
   1600 Amphitheatre Parkway
   Mountain View, CA  94043
   US

   Email: weihaw@google.com




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   Nicolas Lidzborkski
   Google, Inc.
   1600 Amphitheatre Parkway
   Mountain View, CA  94043
   US

   Email: nlidz@google.com


   Elie Bursztein
   Google, Inc.
   1600 Amphitheatre Parkway
   Mountain View, CA  94043
   US

   Email: elieb@google.com



































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