wdiff rfc8689.alt-original rfc8689.txt

Internet Engineering Task Force (IETF) J. Fenton
Internet-Draft
Request for Comments: 8689 Altmode Networks
Intended status:
Category: Standards Track August 2, November 2019
Expires: February 3, 2020
ISSN: 2070-1721

SMTP Require TLS Option
draft-ietf-uta-smtp-require-tls-09

Abstract

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, by default, prioritized over security. This
document describes an SMTP service extension, REQUIRETLS, and a
message header field, TLS-Required. If the REQUIRETLS option or TLS-Required TLS-
Required message header field is used when sending a message, it
asserts a request on the part of the message sender to override the
default negotiation of TLS, either by requiring that TLS be
negotiated when the message is relayed, relayed or by requesting that
recipient-side policy mechanisms such as MTA-STS and DANE DNS-Based
Authentication of Named Entities (DANE) be ignored when relaying a
message for which security is unimportant.

Status of This Memo

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This Internet-Draft will expire on February 3, 2020.
https://www.rfc-editor.org/info/rfc8689.

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Table of Contents

1. Introduction . . . . . . . . . . . . . . . . . . . . . . . . 3
1.1. Requirements Language . . . . . . . . . . . . . . . . . . 4
2. The REQUIRETLS Service Extension . . . . . . . . . . . . . . 4
3. The TLS-Required Header Field . . . . . . . . . . . . . . . . 5
4. REQUIRETLS Semantics . . . . . . . . . . . . . . . . . . . . 6
4.1. REQUIRETLS Receipt Requirements . . . . . . . . . . . . . 6
4.2. REQUIRETLS Sender Requirements . . . . . . . . . . . . . 6
4.2.1. Sending with TLS Required . . . . . . . . . . . . . . 6
4.2.2. Sending with TLS Optional . . . . . . . . . . . . . . 7
4.3. REQUIRETLS Submission . . . . . . . . . . . . . . . . . . 8
4.4. Delivery of REQUIRETLS messages . . . . . . . . . . . . . 8
5. Non-delivery message handling . . . . . . . . . . . . . . . . 8 Message Handling
6. Reorigination considerations . . . . . . . . . . . . . . . . 9 Considerations
7. IANA Considerations . . . . . . . . . . . . . . . . . . . . . 10
8. Security Considerations . . . . . . . . . . . . . . . . . . . 11
8.1. Passive attacks . . . . . . . . . . . . . . . . . . . . . 11 Attacks
8.2. Active attacks . . . . . . . . . . . . . . . . . . . . . 11 Attacks
8.3. Bad Actor Bad-Actor MTAs . . . . . . . . . . . . . . . . . . . . . 12
8.4. Policy Conflicts . . . . . . . . . . . . . . . . . . . . 12
9. Acknowledgements . . . . . . . . . . . . . . . . . . . . . . 12
10. Revision History . . . . . . . . . . . . . . . . . . . . . . 13
10.1. Changes since -08 Draft . . . . . . . . . . . . . . . . 13
10.2. Changes since -07 Draft . . . . . . . . . . . . . . . . 13
10.3. Changes since -06 Draft . . . . . . . . . . . . . . . . 13
10.4. Changes since -05 Draft . . . . . . . . . . . . . . . . 14
10.5. Changes since -04 Draft . . . . . . . . . . . . . . . . 14
10.6. Changes since -03 Draft . . . . . . . . . . . . . . . . 14
10.7. Changes since -02 Draft . . . . . . . . . . . . . . . . 14
10.8. Changes since -01 Draft . . . . . . . . . . . . . . . . 14
10.9. Changes since -00 Draft . . . . . . . . . . . . . . . . 15
10.10. Changes since fenton-03 Draft . . . . . . . . . . . . . 15
10.11. Changes Since -02 Draft . . . . . . . . . . . . . . . . 15
10.12. Changes Since -01 Draft . . . . . . . . . . . . . . . . 15
10.13. Changes Since -00 Draft . . . . . . . . . . . . . . . . 15
11. References . . . . . . . . . . . . . . . . . . . . . . . . . 16
11.1. Normative References . . . . . . . . . . . . . . . . . . 16
11.2. Informative References . . . . . . . . . . . . . . . . . 18
Appendix A. Examples . . . . . . . . . . . . . . . . . . . . . . 19
9. References
9.1. Normative References
9.2. Informative References
Appendix A. Examples
A.1. REQUIRETLS SMTP Option . . . . . . . . . . . . . . . . . 19
A.2. TLS-Required Header Field . . . . . . . . . . . . . . . . 20
Acknowledgements
Author's Address . . . . . . . . . . . . . . . . . . . . . . . . 21

1. Introduction

The SMTP [RFC5321] STARTTLS service extension [RFC3207] provides a
means by which an SMTP server and client can establish a Transport
Layer Security (TLS) protected session for the transmission of email
messages. By default, TLS is used only upon mutual agreement
(successful negotiation) of STARTTLS between the client and server;
if this is not possible, the message is sent without transport
encryption. Furthermore, it is common practice for the client to
negotiate TLS even if the SMTP server's certificate is invalid.

Policy mechanisms such as DANE [RFC7672] and MTA-STS [RFC8461] may
impose requirements for the use of TLS for email destined for some
domains. However, such policies do not allow the sender to specify
which messages are more sensitive and require transport-level
encryption,
encryption and which ones are less sensitive and ought to be relayed
even if TLS cannot be negotiated successfully.

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

REQUIRETLS consists of two mechanisms: an SMTP service extension and
a message header field. The service extension is used to specify
that a given message sent during a particular session MUST be sent
over a TLS-protected session with specified security characteristics.
It also requires that the SMTP server advertise that it supports
REQUIRETLS, in effect promising that it will honor the requirement to
enforce TLS transmission and REQUIRETLS support for onward
transmission of those messages.

The TLS-Required message header field is used to convey a request to
ignore recipient-side policy mechanisms such as MTA-STS and DANE,
thereby prioritizing delivery over ability to negotiate TLS. Unlike
the service extension, the TLS-Required header field allows the
message to transit through one or more MTAs that do not support
REQUIRETLS.

1.1. 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.

The formal syntax uses the Augmented Backus-Naur Form (ABNF)
[RFC5234]
[RFC5234], including the core rules defined in Appendix B of that
document.

2. The REQUIRETLS Service Extension

The REQUIRETLS SMTP service extension has the following
characteristics:

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

2. The EHLO keyword value associated with this extension is
"REQUIRETLS".

3. No additional SMTP verbs are defined by this extension.

4. One optional parameter ("REQUIRETLS") is added to the MAIL FROM
command by this extension. No value is associated with this
parameter.

5. The maximum length of a MAIL FROM command line is increased by 11
octets by the possible addition of a space and the REQUIRETLS
keyword.

6. One new SMTP status code is defined by this extension to convey
an error condition resulting from failure of the client to send
data to a server that does not also supporting support the REQUIRETLS
extension.

7. The REQUIRETLS extension is valid for message relay [RFC5321],
submission [RFC6409], and the Local Mail Transfer Protocol (LMTP)
[RFC2033]
[RFC2033].

8. The ABNF syntax for the MAIL FROM parameter is as follows:

requiretls-param = "REQUIRETLS"
; where requiretls-param is an instance of an
; esmtp-param used in Mail-parameters in
; RFC 5321 5321, Section 4.1.2. There is no esmtp-value
; associated with requiretls-param.

In order to specify REQUIRETLS treatment for a given message, the
REQUIRETLS option is specified on in the MAIL FROM command when that
message is transmitted. This option MUST only be specified in the
context of an SMTP session meeting the security requirements of
REQUIRETLS:

* The session itself MUST employ TLS transmission.

* If the SMTP server to which the message is being transmitted is
identified through an MX record lookup, its name MUST be validated
via a DNSSEC signature on the recipient domain's MX record, or the
MX hostname MUST be validated by an MTA-STS policy as described in
Section 4.1 of RFC 8461 [RFC8461]. DNSSEC is defined in RFC 4033 [RFC4033], RFC 4034
[RFC4034], and RFC 4035 [RFC4035].

* The certificate presented by the SMTP server MUST either verify MUST be
verified successfully in by a trust chain leading to a certificate
trusted by the SMTP client client, or it MUST verify be verified successfully
using DANE DANE, as specified in RFC 7672 [RFC7672]. For trust chains, the
choice of trusted (root) certificates is at the discretion of the
SMTP client.

* Following the negotiation of STARTTLS, the SMTP server MUST
advertise in the subsequent EHLO response that it supports
REQUIRETLS.

3. The TLS-Required Header Field

One new message header field [RFC5322], TLS-Required, is defined by
this specification. It is used for messages for which the originator
requests that the recipient TLS policy (including MTA-STS [RFC8461]
and DANE [RFC7672]) be ignored. This might be done, for example, to
report a misconfigured mail server, such as an expired TLS
certificate.

The TLS-Required header field has a single REQUIRED parameter:

* No - The SMTP client SHOULD attempt to send the message regardless
of its ability to negotiate STARTTLS with the SMTP server,
ignoring policy-based mechanisms (including MTA-STS and DANE), if
any, asserted by the recipient domain. Nevertheless, the client
SHOULD negotiate STARTTLS with the server if available.

More than one instance of the TLS-Required header field MUST NOT
appear in a given message.

The ABNF syntax for the TLS-Required header field is as follows:

requiretls-field = "TLS-Required:" [FWS] "No" CRLF
; where requiretls-field in an instance of an
; optional-field defined in RFC 5322 5322, Section
; 3.6.8.
FWS = <as defined in RFC 5322>
CRLF = <as defined in RFC 5322>

4. REQUIRETLS Semantics

4.1. REQUIRETLS Receipt Requirements

Upon receipt of the REQUIRETLS option on a MAIL FROM command during
the receipt of a message, an SMTP server MUST tag that message as
needing REQUIRETLS handling.

Upon receipt of a message not specifying the REQUIRETLS option on its
MAIL FROM command but containing the TLS-Required header field in its
message header, an SMTP server implementing this specification MUST
tag that message with the option specified in the TLS-Required header
field. If the REQUIRETLS MAIL FROM parameter is specified, the TLS-
Required header field MUST be ignored but MAY be included in the
onward relay of the message.

The manner in which the above tagging takes place is implementation- implementation
dependent. If the message is being locally aliased and redistributed
to multiple addresses, all instances of the message MUST be tagged in
the same manner.

4.2. REQUIRETLS Sender Requirements

4.2.1. Sending with TLS Required

When sending a message tagged as requiring TLS for which the MAIL
FROM return-path is not empty (an empty MAIL FROM return-path
indicating a bounce message), the sending (client) MTA MUST:

1. Look up the SMTP server to which the message is to be sent sent, as
described in [RFC5321] [RFC5321], Section 5.1.

2. If the server lookup is accomplished via the recipient domain's
MX record (the usual case) and is not accompanied by a valid
DNSSEC signature, the client MUST also validate the SMTP server
name using MTA-STS MTA-STS, as described in RFC 8461 [RFC8461] [RFC8461], Section 4.1.

3. Open an SMTP session with the peer SMTP server using the EHLO
verb.

4. Establish a TLS-protected SMTP session with its peer SMTP server
and authenticate the server's certificate as specified in
[RFC6125] or [RFC7672] [RFC7672], as applicable. The hostname from the MX
record lookup (or the domain name in the absence of an MX record
where an A record is used directly) MUST match the DNS-ID or CN-
ID of the certificate presented by the server.

5. Ensure that the response to the subsequent EHLO following
establishment of the TLS protection advertises the REQUIRETLS
capability.

The SMTP client SHOULD follow the recommendations in [RFC7525] or its
successor with respect to negotiation of the TLS session.

If any of the above steps fail, the client MUST issue a QUIT to the
server and repeat steps 2-5 with each host on the recipient domain's
list of MX hosts in an attempt to find a mail path that meets the
sender's requirements. The client MAY send other, unprotected, unprotected
messages to that server if it has any such messages prior to issuing
the QUIT. If there are no more MX hosts, the client MUST NOT
transmit the message to the domain.

Following such a failure, the SMTP client MUST send a non-delivery
notification to the reverse-path of the failed message message, as described
in section Section 3.6 of [RFC5321]. The following status codes [RFC5248]
SHOULD be used:

* REQUIRETLS not supported by server: 5.7.YYY 5.7.30 REQUIRETLS needed

o support
required

* Unable to establish TLS-protected SMTP session: 5.7.10 Encryption
needed

Refer to Section 5 for further requirements regarding non-delivery
messages.

If all REQUIRETLS requirements have been met, transmit the message,
issuing the REQUIRETLS option on the MAIL FROM command with the
required option(s), if any.

4.2.2. Sending with TLS Optional

Messages tagged TLS-Required: No "TLS-Required: No" are handled as follows. When
sending such a message, the sending (client) MTA MUST:

* Look up the SMTP server to which the message is to be sent sent, as
described in [RFC5321] [RFC5321], Section 5.1.

* Open an SMTP session with the peer SMTP server using the EHLO
verb. Attempt to negotiate STARTTLS if possible, and follow any
policy published by the recipient domain, but do not fail if this
is unsuccessful.

Some SMTP servers may be configured to require STARTTLS connections
as a matter of policy and not accept messages in the absence of
STARTTLS. A non-delivery notification MUST be returned to the sender
if message relay fails due to an inability to negotiate STARTTLS when
required by the server.

Since messages tagged with TLS-Required: No "TLS-Required: No" will sometimes be sent
to SMTP servers not supporting REQUIRETLS, that option will not be
uniformly observed by all SMTP relay hops.

4.3. REQUIRETLS Submission

An MUA

A Mail User Agent (MUA) or other agent making the initial
introduction of a message has the option to decide whether to require
TLS. If TLS is to be required, it MUST do so by negotiating STARTTLS
and REQUIRETLS and
include including the REQUIRETLS option on the MAIL FROM
command, as is done for message relay.

When TLS is not to be required, the sender MUST include the TLS-
Required header field in the message. SMTP servers implementing this
specification MUST interpret this header field as described in
Section 4.1.

In either case, the decision whether to specify REQUIRETLS MAY be
done based on a user interface selection or based on a ruleset or
other policy. The manner in which the decision to require TLS is
made is implementation-dependent implementation dependent and is beyond the scope of this
specification.

4.4. Delivery of REQUIRETLS messages

Messages are usually retrieved by end users using protocols other
than SMTP such as IMAP [RFC3501], POP [RFC1939], or web Web mail systems.
Mail delivery agents supporting the REQUIRETLS SMTP option SHOULD
observe the guidelines in [RFC8314].

5. Non-delivery message handling Message Handling

Non-delivery ("bounce") messages usually contain important metadata
about the message to which they refer, including the original message
header. They therefore MUST be protected in the same manner as the
original message. All non-delivery messages resulting from messages
with the REQUIRETLS SMTP option, whether resulting from a REQUIRETLS
error or some other, other issue, MUST also specify the REQUIRETLS SMTP
option unless redacted as described below.

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 requiring TLS are advised to make
sure that they are capable of receiving mail using REQUIRETLS as
well. Otherwise, such non-delivery messages will be lost.

If a REQUIRETLS message is bounced, the server MUST behave as if
RET=HDRS was present present, as described in [RFC3461]. If both RET=FULL
and REQUIRETLS are present, the RET=FULL MUST be disregarded. The
SMTP client for a REQUIRETLS bounce message uses an empty MAIL FROM
return-path
return-path, as required by [RFC5321]. When the MAIL FROM return-path return-
path is empty, the REQUIRETLS parameter SHOULD NOT cause a bounce
message to be discarded even if the next-hop relay does not advertise
REQUIRETLS.

Senders of messages requiring TLS are advised to consider the
possibility that bounce messages will be lost as a result of
REQUIRETLS return path failure, failure and that some information could be
leaked if a bounce message is not able to be transmitted with
REQUIRETLS.

6. Reorigination considerations Considerations

In a number of situations, a mediator [RFC5598] originates a new
message as a result of an incoming message. These situations
include, include
but are not limited to, to mailing lists (including administrative
traffic such as message approval requests), Sieve [RFC5228],
"vacation" responders, and other filters to which incoming messages
may be piped. These newly originated messages may essentially be
copies of the incoming message, such as with a forwarding service or
a mailing list expander. In other cases, such as with a vacation
message or a delivery notification, they will be different but might
contain parts of the original message or other information for which
the original message sender wants to influence the requirement to use
TLS transmission.

Mediators that reoriginate messages should apply REQUIRETLS
requirements in incoming messages (both requiring TLS transmission
and requesting that TLS not be required) to the reoriginated messages
to the extent feasible. A limitation to this might be that for a
message requiring TLS, redistribution to multiple addresses while
retaining the TLS requirement could result in the message not being
delivered to some of the intended recipients.

User-side mediators (such as use of Sieve rules on a user agent)
typically do not have access to the SMTP details, details and therefore may
not be aware of the REQUIRETLS requirement on a delivered message.
Recipients that expect sensitive traffic should avoid the use of
user-side mediators. Alternatively, if operationally feasible (such
as when forwarding to a specific, known address), they should apply
REQUIRETLS to all reoriginated messages that do not contain the "TLS-
Required: No" header field.

7. IANA Considerations

If published as an RFC,

Per this draft requests the addition of document, IANA has added the following keyword to the SMTP "SMTP
Service Extensions Registry Extensions" subregistry of the "Mail Parameters" registry
[MailParams]:

Textual name: Require TLS

EHLO keyword value: Keyword: REQUIRETLS
Description: Require TLS
Syntax and parameters: (no parameters)
Additional SMTP verbs: none
MAIL and RCPT parameters: REQUIRETLS parameter on MAIL
Behavior: Use of the REQUIRETLS parameter on
the MAIL verb causes that message to
require the use of TLS and tagging
with REQUIRETLS for all onward
relay.
Command length increment: 11 characters

If published as an RFC,

Per this draft requests the addition of document, IANA has added an entry to the Simple "Enumerated Status
Codes" subregistry of the "Simple Mail Transfer Protocol (SMTP)
Enhanced Status Codes
Registry Registry" [SMTPStatusCodes]:

Code: 5.7.YYY X.7.30
Sample Text: REQUIRETLS support required
Associated basic status code: 550
Description: This indicates that the message was
not able to be forwarded because it
was received with a REQUIRETLS
requirement and none of the SMTP
servers to which the message should
be forwarded provide this support.
Reference: (this document) RFC 8689
Submitter: J. Fenton
Change controller: Controller: IESG

If published as an RFC,

Per this draft requests the addition of document, IANA has added an entry to the Permanent "Permanent Message
Header Field Names Registry
[PermMessageHeaderFields]: Names" subregistry of the "Message Headers" registry
[MessageHeaders] as follows:

Header field name: TLS-Required
Applicable protocol: mail
Status: standard
Author/change controller: IETF
Specification document: (this document)

This section is to be updated for publication by the RFC Editor. 8689

8. Security Considerations

The purpose of REQUIRETLS is to give the originator of a message
control over the security of email they send, either by conveying an
expectation that it will be transmitted in an encrypted form "over over the wire"
wire or explicitly indicating that transport encryption is not
required if it cannot be successfully negotiated.

The following considerations apply to the REQUIRETLS service
extension but not the TLS-Required header field, since messages
specifying the header field are less concerned with transport
security.

8.1. Passive attacks Attacks

REQUIRETLS is generally effective against passive attackers who are
merely trying to eavesdrop on an SMTP exchange between an SMTP client
and server. This assumes, of course, the cryptographic integrity of
the TLS connection being used.

8.2. Active attacks Attacks

Active attacks against TLS encrypted TLS-encrypted SMTP connections can take many
forms. One such attack is to interfere in the negotiation by
changing the STARTTLS command to something illegal such as XXXXXXXX.
This causes TLS negotiation to fail and messages to be sent in the
clear, where they can be intercepted. REQUIRETLS detects the failure
of STARTTLS and declines to send the message rather than send it
insecurely.

A second form of attack is a man-in-the-middle attack where the
attacker terminates the TLS connection rather than the intended SMTP
server. This is possible when, as is commonly the case, the SMTP
client either does not verify the server's certificate or establishes
the connection even when the verification fails. REQUIRETLS requires
successful certificate validation before sending the message.

Another active attack involves the spoofing of DNS MX records of the
recipient domain. An attacker having with this capability could potentially
cause the message to be redirected to a mail server under the
attacker's own control, which would presumably have a valid
certificate. REQUIRETLS requires that the recipient domain's MX
record lookup be validated either using DNSSEC or via a published
MTA-STS policy that specifies the acceptable SMTP server hostname(s)
for the recipient domain.

8.3. Bad Actor Bad-Actor MTAs

A bad-actor MTA along the message transmission path could
misrepresent its support of REQUIRETLS and/or actively strip
REQUIRETLS tags from messages it handles. However, since
intermediate MTAs are already trusted with the cleartext of messages
they handle, and are not part of the threat model for transport-layer
security, they are also not part of the threat model for REQUIRETLS.

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 [RFC8551].

8.4. Policy Conflicts

In some cases, the use of the TLS-Required header field may conflict
with a recipient domain policy expressed through the DANE [RFC7672]
or MTA-STS [RFC8461] protocols. Although these protocols encourage
the use of TLS transport by advertising the availability of TLS, the
use of the "TLS-Required: No" header field represents an explicit
decision on the part of the sender not to require the use of TLS,
such as to overcome a configuration error. The recipient domain has
the ultimate ability to require TLS by not accepting messages when
STARTTLS has not been negotiated; otherwise, "TLS-Required: No" is
effectively directing the client MTA to behave as if it does not
support DANE nor or MTA-STS.

11.

9. References

11.1.

9.1. Normative References

[MailParams]
Internet Assigned Numbers Authority (IANA), "IANA Mail
IANA, "Mail Parameters", 2007,
<http://www.iana.org/assignments/mail-parameters>.

[PermMessageHeaderFields]
Internet Assigned Numbers Authority (IANA),

[MessageHeaders]
IANA, "Permanent Message Header Field Names Registry", 2004,
<https://www.iana.org/assignments/message-headers/
message-headers.xhtml#perm-headers>. Names",
<https://www.iana.org/assignments/message-headers>.

[RFC2119] Bradner, S., "Key words for use in RFCs to Indicate
Requirement Levels", BCP 14, RFC 2119,
DOI 10.17487/RFC2119, March 1997,
<https://www.rfc-editor.org/info/rfc2119>.

[RFC3207] Hoffman, P., "SMTP Service Extension for Secure SMTP over
Transport Layer Security", RFC 3207, DOI 10.17487/RFC3207,
February 2002, <https://www.rfc-editor.org/info/rfc3207>.

[RFC3461] Moore, K., "Simple Mail Transfer Protocol (SMTP) Service
Extension for Delivery Status Notifications (DSNs)",
RFC 3461, DOI 10.17487/RFC3461, January 2003,
<https://www.rfc-editor.org/info/rfc3461>.

[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,
<https://www.rfc-editor.org/info/rfc4033>.

[RFC4034] Arends, R., Austein, R., Larson, M., Massey, D., and S.
Rose, "Resource Records for the DNS Security Extensions",
RFC 4034, DOI 10.17487/RFC4034, March 2005,
<https://www.rfc-editor.org/info/rfc4034>.

[RFC4035] Arends, R., Austein, R., Larson, M., Massey, D., and S.
Rose, "Protocol Modifications for the DNS Security
Extensions", RFC 4035, DOI 10.17487/RFC4035, March 2005,
<https://www.rfc-editor.org/info/rfc4035>.

[RFC5234] Crocker, D., Ed. and P. Overell, "Augmented BNF for Syntax
Specifications: ABNF", STD 68, RFC 5234,
DOI 10.17487/RFC5234, January 2008,
<https://www.rfc-editor.org/info/rfc5234>.

[RFC5248] Hansen, T. and J. Klensin, "A Registry for SMTP Enhanced
Mail System Status Codes", BCP 138, RFC 5248,
DOI 10.17487/RFC5248, June 2008,
<https://www.rfc-editor.org/info/rfc5248>.

[RFC5321] Klensin, J., "Simple Mail Transfer Protocol", RFC 5321,
DOI 10.17487/RFC5321, October 2008,
<https://www.rfc-editor.org/info/rfc5321>.

[RFC5322] Resnick, P., Ed., "Internet Message Format", RFC 5322,
DOI 10.17487/RFC5322, October 2008,
<https://www.rfc-editor.org/info/rfc5322>.

[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, DOI 10.17487/RFC6125, March
2011, <https://www.rfc-editor.org/info/rfc6125>.

[RFC7525] Sheffer, Y., Holz, R., and P. Saint-Andre,
"Recommendations for Secure Use of Transport Layer
Security (TLS) and Datagram Transport Layer Security
(DTLS)", BCP 195, RFC 7525, DOI 10.17487/RFC7525, May
2015, <https://www.rfc-editor.org/info/rfc7525>.

[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,
<https://www.rfc-editor.org/info/rfc7672>.

[RFC8174] Leiba, B., "Ambiguity of Uppercase vs Lowercase in RFC
2119 Key Words", BCP 14, RFC 8174, DOI 10.17487/RFC8174,
May 2017, <https://www.rfc-editor.org/info/rfc8174>.

[RFC8314] Moore, K. and C. Newman, "Cleartext Considered Obsolete:
Use of Transport Layer Security (TLS) for Email Submission
and Access", RFC 8314, DOI 10.17487/RFC8314, January 2018,
<https://www.rfc-editor.org/info/rfc8314>.

[RFC8461] Margolis, D., Risher, M., Ramakrishnan, B., Brotman, A.,
and J. Jones, "SMTP MTA Strict Transport Security (MTA-
STS)", RFC 8461, DOI 10.17487/RFC8461, September 2018,
<https://www.rfc-editor.org/info/rfc8461>.

[SMTPStatusCodes]
Internet Assigned Numbers Authority (IANA),
IANA, "Simple Mail Transfer Protocol (SMTP) Enhanced
Status Codes Registry",
2008, <http://www.iana.org/assignments/ <https://www.iana.org/assignments/
smtp-enhanced-status-codes>.

11.2.

9.2. Informative References

[RFC1939] Myers, J. and M. Rose, "Post Office Protocol - Version 3",
STD 53, RFC 1939, DOI 10.17487/RFC1939, May 1996,
<https://www.rfc-editor.org/info/rfc1939>.

[RFC2033] Myers, J., "Local Mail Transfer Protocol", RFC 2033,
DOI 10.17487/RFC2033, October 1996,
<https://www.rfc-editor.org/info/rfc2033>.

[RFC3501] Crispin, M., "INTERNET MESSAGE ACCESS PROTOCOL - VERSION
4rev1", RFC 3501, DOI 10.17487/RFC3501, March 2003,
<https://www.rfc-editor.org/info/rfc3501>.

[RFC4880] Callas, J., Donnerhacke, L., Finney, H., Shaw, D., and R.
Thayer, "OpenPGP Message Format", RFC 4880,
DOI 10.17487/RFC4880, November 2007,
<https://www.rfc-editor.org/info/rfc4880>.

[RFC5228] Guenther, P., Ed. and T. Showalter, Ed., "Sieve: An Email
Filtering Language", RFC 5228, DOI 10.17487/RFC5228,
January 2008, <https://www.rfc-editor.org/info/rfc5228>.

[RFC5598] Crocker, D., "Internet Mail Architecture", RFC 5598,
DOI 10.17487/RFC5598, July 2009,
<https://www.rfc-editor.org/info/rfc5598>.

[RFC6409] Gellens, R. and J. Klensin, "Message Submission for Mail",
STD 72, RFC 6409, DOI 10.17487/RFC6409, November 2011,
<https://www.rfc-editor.org/info/rfc6409>.

[RFC8551] Schaad, J., Ramsdell, B., and S. Turner, "Secure/
Multipurpose Internet Mail Extensions (S/MIME) Version 4.0
Message Specification", RFC 8551, DOI 10.17487/RFC8551,
April 2019, <https://www.rfc-editor.org/info/rfc8551>.

Appendix A. Examples

This section is informative.

A.1. REQUIRETLS SMTP Option

The TLS-Required SMTP option is used to express the intent intention of the
sender that to have the associated message be relayed using TLS. In the
following example, lines beginning with C: "C:" are transmitted from the
SMTP client to the server, and lines beginning with S: "S:" are
transmitted in the opposite direction.

(at this point TLS negotiation takes place. The remainder of this
session occurs within TLS.)

S: 220 mail.example.net ESMTP
C: EHLO mail.example.org
S: 250-mail.example.net Hello example.org [192.0.2.1]
S: 250-SIZE 52428800
S: 250-8BITMIME
S: 250-PIPELINING
S: 250-REQUIRETLS
S: 250 HELP
C: MAIL FROM:<roger@example.org> REQUIRETLS
S: 250 OK
C: RCPT TO:<editor@example.net>
S: 250 Accepted
C: DATA
S: 354 Enter message, ending with "." on a line by itself

(message follows)

C: .
S: 250 OK
C: QUIT

A.2. TLS-Required Header Field

The TLS-Required header field is used when the sender requests that
the mail system not heed a default policy of the recipient domain
requiring TLS. It might be used, for example, to allow problems with
the recipient domain's TLS certificate to be reported:

From: Roger Reporter <roger@example.org>
To: Andy Admin <admin@example.com>
Subject: Certificate problem?
TLS-Required: No
Date: Fri, 18 Jan 2019 10:26:55 -0800
Message-ID: <5c421a6f79c0e_d153ff8286d45c468473@mail.example.org>

Andy, there seems to be a problem with the TLS certificate
on your mail server. Are you aware of this?

Roger

Acknowledgements

The author would like to acknowledge many helpful suggestions on the
ietf-smtp and uta mailing lists, in particular those of Viktor
Dukhovni, Chris Newman, Tony Finch, Jeremy Harris, Arvel Hathcock, John Klensin,
Barry Leiba, John Levine, Chris Newman, Rolf Sonneveld, and Per
Thorsheim.

Author's Address

Jim Fenton
Altmode Networks
Los Altos, California 94024
USA
United States of America

Email: fenton@bluepopcorn.net