Internet-Draft DKIM Anti-Replay Canonicalization December 2022
Kucherawy Expires 1 July 2023 [Page]
Network Working Group
Intended Status:
M. S. Kucherawy, Ed.

Replay-Resistant DomainKeys Identified Mail (DKIM) Signatures


DomainKeys Identified Mail (DKIM) provides a digital signature mechanism for Internet messages, allowing a domain name owner to affix its domain name in a way that can be cryptographically validated.

DKIM signatures protect the integrity of the message header and body only. By design, it decoupled itself from the transport and storage mechanisms used to handle messages. This gives rise to a possible replay attack, which the original DKIM specification acknowledged but did not provide a mitigation strategy. This document presents an optional method for binding a signature to a specific recipient or set of recipients so that broader replay attacks can be mitigated.

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This Internet-Draft will expire on 1 July 2023.

Table of Contents

1. Introduction

DomainKeys Identified Mail (DKIM) provides a digital signature mechanism for Internet messages, allowing a domain name owner to affix its domain name to a message in a way that can be cryptographically validated so long as the integrity of the message is preserved in transit.

[RFC4686] presents the original threat model DKIM was meant to address, and the environment in which it was expected to work. Notably, DKIM decoupled itself from the transport of the message. The theory suggests it should be possible to validate a signature whether a message is in situ (i.e., in an inbox on disk), in transit between mail servers, or being retrieved through a mailbox access protocol.

In particular, this meant a DKIM signature can validate irrespective of what is in the SMTP [RFC5321] envelope containing it, or even when there is no envelope to consider. This means a message and its signature can be re-sent to anyone simply by changing the set of recipients in the envelope and passing the message back to a Mail Transport Agent (MTA) or Mail Submission Agent (MSA). As the message itself is unaltered, any DKIM signature(s) on it will continue to validate. This is a form of replay attack, and it relies for its success on the perceived value (i.e., reputation) of the domain(s) named in the signature(s).

This document describes a mechanism by which a signature and a message can be coupled such that successful replays to other recipient sets are not possible, as the signature will no longer validate.

2. Definitions

Several terms used in this document are based on their definitions in [RFC5598].

The term "envelope recipient" is, using the notation proposed in that document, an RFC5321.RcptTo address.

2.2. Requirements Language

The key words "MUST", "MUST NOT", "REQUIRED", "SHALL", "SHALL NOT", "SHOULD", "SHOULD NOT", "RECOMMENDED", "NOT RECOMMENDED", "MAY", and "OPTIONAL" in this document are to be interpreted as described in BCP 14 [RFC2119] [RFC8174] when, and only when, they appear in all capitals, as shown here.

3. The 'e' Tag

3.1. Syntax

Using ABNF [RFC5234], the syntax for the new tag is:

    sig-e-tag = %x65 [FWS] "=" %x79

3.2. General Definition

This section introduces the "e" (for "envelope") tag, a new DKIM signature tag that can be used by a signer to indicate that signature will only validate for a specific envelope recipient set, namely the one associated with the message at the time it was signed.

DKIM signers and verifiers to date have no reason to be interested in any aspect of the envelope used to transport a message. This sort of verification is not possible without that context being available, which may prove to be a challenge to some operating environments. Also, this will make it impossible to validate a DKIM signature using this algorithm in a context where no envelope exists, such as when retrieving a message from a mailbox.

The expected value of the tag is simply the character "y", though other values may be introduced by future work. The value has no particular meaning; the presence of the tag is the important signal.

[FOR DISCUSSION] Maybe this should be "r", indicating "recipients", to allow later extensions to include other parts of the envelope that might be helpful to include.

The presence of this tag in a DKIM signature indicates that the signer executed a modified version of the algorithm described in Section 3.7 of [RFC6376], and the verifier MUST do the same. The modification inserts the envelope recipients available at signing or verification time into the data fed to the hash algorithm to either produce or verify the DKIM signature.

3.2.1. Modified Algorithm

This section specifies the modified version of the algorithm defined in Section 3.7 of [RFC6376].

The pseudo-code of "data-hash" is replaced as follows:


    data-hash = hash-alg (h-headers, D-SIG, body-hash)


    data-hash = hash-alg (recipients, h-headers, D-SIG, body-hash)

The definition of "data-hash" is replaced as follows:


    data-hash: is the output from using the hash-alg algorithm, to hash
               the header including the DKIM-Signature header, and the
               body hash.


    data-hash: is the output from using the hash-alg algorithm to hash
               the recipients, the header including the DKIM-Signature
               header field, and the body hash.

"recipients" is determined as follows:

  1. Collect all envelope recipients into a list.
  2. Remove any duplicate entries in the list.
  3. Sort them in typical lexical ASCII order.
  4. Format the list by concatenating them all in this sorted order, separated by CRLF strings (ASCII 13 followed by ASCII 10), and with the last one terminated by a CRLF.

The signing and verifying processes defined for DKIM are otherwise unmodified.

3.3. Example

Consider the following SMTP transaction, wherein "C" denotes something sent by an SMTP client, "S" denotes something sent by an SMTP server, and terminating CRLFs in both directions are omitted:

  S: 250 Sender OK
  C: RCPT TO:<>
  S: 250 Recipient OK
  C: RCPT TO:<>
  S: 250 Recipient OK
  S: 354 Go ahead
  [message header omitted]

  [message body omitted]
  C: 250 Message delivered

Compared to the standard signatures that would be generated or verified in the absence of this tag, the process described above would work the same way as the standard signing process would, except that the content fed to the hash algorithm would be preceded by:<CR><LF><CR><LF>

4. Discussion

Use of this tag guarantees that a signature will not verify unless sent to exactly the same set of envelope recipients as was present in the envelope when the message was prepared for signing. The fact that the recipient set is sorted allows verifiers to tolerate any reordering of the envelope that may be done in transit. However, if any original recipient is removed, or any new recipient is added, the signature will not validate because the content passed to the hash step at the verifier will differ from what was done at the signer. Thus, in the replay scenario described in Section 1, the signature no longer validates.

Anecdotal evidence suggests that the bulk of Internet message traffic is single-recipient traffic already, which implies the success of this proposal. However, since the messaging standards both permit and even encourage this "common factoring" of traffic (see Section of [RFC5321]), and this evidence has not been broadly verified, it is appropriate to consider all possibilities.

In the absence of an SMTP envelope in the verification environment, the DKIM implementation SHOULD indicate that the signature cannot be verified, as distinct from considering such validation to have failed. Legacy implementations may not be capable of this, however.

If the need to be able to validate a signature from storage (without an envelope) needs to be preserved, the signer can still add a second signature not using this tag, which therefore does not need the envelope context to verify. This, however, requires the verifier to understand when it is appropriate to use which signature and how to interpret their results. There may be a solution in this space via use or extension of the Authentication-Results header field [RFC8601].

Since [RFC6376] stipulates that unknown tags are to be ignored, there will be a possibly substantial time period during which the tag is unknown to receivers. Legacy verifiers will thus ignore the tag but still process the signature, leading to a failure result. Operators should thus expect these signatures to fail broadly during any early deployment period, even for non-replay messages, and it may be some time before meaningful signal begins to appear.

Note that this mechanism is fragile in the modern Internet message ecosystem. Some scenarios that will yield false negatives with this method are described in subsections below. Analysis has shown that it is likely beneficial to include both a conventional DKIM signature and one using this modification on a message. This produces additional signal, rather than interfering with the signal previously available. See Appendix A for further discussion.

4.1. Recipient Mutations

If a receiving MTA notes that one of the envelope recipients refers to a mailbox in a domain for which it has administrative authority, but is known to be an alias, it may rewrite that envelope into its canonical form. For instance, if a receiving MTA is officially known as the mail server for "", but also accepts mail for its users when addressed to "", it may alter that latter address in the envelope to refer to its canonical name. This alters the recipient list, and thus alters the content passed to the hash algorithm when validating the signature, leading to a failure.

Since hostnames are generally case-insensitive on the Internet, a relay MTA might (improperly) fold a hostname to lowercase. This too would invalidate a signature making use of this protocol.

[FOR DISCUSSION] A mitigation strategy here would be to pass the domain part of the address after converting it all to lowercase.

4.2. Envelope Splitting

If a message contains envelope recipients at domains served by separate MTAs, [RFC5321] compels the handling MTA to split the message, creating multiple envelopes with different recipient subsets yet identical header and body content. The first of these will be addressed to one recipient and sent on its way; the second will be addressed to another and sent via its own route; etc.

Upon arrival at a DKIM verifier, the recipient list has effectively been altered since signing. This alters the content passed to the hash algorithm when validating the signature, leading to a failure.

This can be avoided by arranging that no envelope ever has more than a single recipient, but this renders useless an important "common factoring" feature of SMTP. In the case of a mailing list server that may need to distribute a single message to a very large number of recipients, this method can impose significant compute or storage costs.

5. IANA Considerations

IANA is asked to make the following entry in the "DKIM-Signature Tag Specifications" sub-registry of the "DKIM Parameters" registry group:

[this document]

6. Security Considerations

All of the security considerations of [RFC6376] apply when applying the modification described here.

A signer that is forced to generate independently signed messages for each recipient in a situation where large recipient lists are common could be exploited to cause a denial-of-service attack simply from the fact that there is an amplication of work being done.

The loss of the ability to verify messages signed using this tag when extracted from their mailboxes will have unknown security impact. Although DKIM intentionally supports this capability, it is not known whether it is widely used.

7. References

7.1. Normative References

Bradner, S. and RFC Publisher, "Key words for use in RFCs to Indicate Requirement Levels", BCP 14, RFC 2119, DOI 10.17487/RFC2119, , <>.
Crocker, D., Ed., Overell, P., and RFC Publisher, "Augmented BNF for Syntax Specifications: ABNF", STD 68, RFC 5234, DOI 10.17487/RFC5234, , <>.
Klensin, J. and RFC Publisher, "Simple Mail Transfer Protocol", RFC 5321, DOI 10.17487/RFC5321, , <>.
Crocker, D., Ed., Hansen, T., Ed., Kucherawy, M., Ed., and RFC Publisher, "DomainKeys Identified Mail (DKIM) Signatures", STD 76, RFC 6376, DOI 10.17487/RFC6376, , <>.
Leiba, B. and RFC Publisher, "Ambiguity of Uppercase vs Lowercase in RFC 2119 Key Words", BCP 14, RFC 8174, DOI 10.17487/RFC8174, , <>.

7.2. Informative References

Fenton, J. and RFC Publisher, "Analysis of Threats Motivating DomainKeys Identified Mail (DKIM)", RFC 4686, DOI 10.17487/RFC4686, , <>.
Crocker, D. and RFC Publisher, "Internet Mail Architecture", RFC 5598, DOI 10.17487/RFC5598, , <>.
Kucherawy, M. and RFC Publisher, "Message Header Field for Indicating Message Authentication Status", RFC 8601, DOI 10.17487/RFC8601, , <>.

Appendix A. Multiple Signatures

The email ecosystem has seen broad adoption of DKIM to date. This means validating signatures already provide useful signal in many cases, and an important property of DKIM is that this signal survives changes to the message envelope that might occur as described in Section 4.

Switching to this proposal would solve the replay problem at the expense of DKIM's broader success to date. Naturally, this is not desirable.

Analysis suggests that a hybrid approach is possible. That is: A signer affixes a typical "pure" DKIM signature and then in addition adds one using this proposal. If we call these signatures A and B, respectively, then there is no loss of signal, only a gain, as follows:

  |   A  |   B  | Meaning                                        |
  | fail | fail | No conclusions possible                        |
  | fail | pass | Should never occur                             |
  | pass | fail | Message arrived intact; may have been replayed |
  | pass | pass | Message arrived intact and was not replayed    |

In particular, if the experimental signature fails while the conventional one does not, we cannot make a conclusion about replay, but all of the original signal provided by the conventional signature is still available. However, if both signatures pass, we are certain no replay occurred.

Appendix B. Acknowledgments

The author wishes to thank Dave Crocker for his contributions to this work.

Author's Address

Murray S. Kucherawy (editor)