Network Working Group K. Moore
Internet-Draft Network Heretics
Updates: 1939, 2595, 3464, 3501, 5068, C. Newman
6186, 6409 (if approved) Oracle
Intended status: Standards Track July 3, 2017
Expires: January 4, 2018
Cleartext Considered Obsolete: Best Current Practices for Use of TLS for
Email Submission and Access
draft-ietf-uta-email-deep-07
Abstract
This specification outlines best current practices for use of
Transport Layer Security (TLS) to provide confidentiality of email
traffic between a mail user agent (MUA) and a mail submission or mail
access server.
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 http://datatracker.ietf.org/drafts/current/.
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 January 4, 2018.
Copyright Notice
Copyright (c) 2017 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
(http://trustee.ietf.org/license-info) in effect on the date of
publication of this document. Please review these documents
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
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the Trust Legal Provisions and are provided without warranty as
described in the Simplified BSD License.
Table of Contents
1. Introduction . . . . . . . . . . . . . . . . . . . . . . . . 3
2. Conventions and Terminology Used in This Document . . . . . . 3
3. Implicit TLS . . . . . . . . . . . . . . . . . . . . . . . . 4
3.1. Implicit TLS for POP . . . . . . . . . . . . . . . . . . 5
3.2. Implicit TLS for IMAP . . . . . . . . . . . . . . . . . . 5
3.3. Implicit TLS for SMTP Submission . . . . . . . . . . . . 5
3.4. Implicit TLS Connection Closure for POP, IMAP and SMTP
Submission . . . . . . . . . . . . . . . . . . . . . . . 6
4. Best Current Practices for Use of TLS by Mail Access
Services and Message Submission Services . . . . . . . . . . 6
4.1. Deprecation of Services Using Cleartext and TLS Versions
< 1.1 . . . . . . . . . . . . . . . . . . . . . . . . . . 7
4.2. Mail Server Use of Client Certificate Authentication . . 8
4.3. Recording TLS Cipher Suite in Received Header . . . . . . 9
4.4. TLS Server Certificate Requirements . . . . . . . . . . . 9
4.5. Recommended DNS records for mail protocol servers . . . . 9
4.5.1. MX records . . . . . . . . . . . . . . . . . . . . . 10
4.5.2. SRV records . . . . . . . . . . . . . . . . . . . . . 10
4.5.3. DNSSEC . . . . . . . . . . . . . . . . . . . . . . . 10
4.5.4. TLSA records . . . . . . . . . . . . . . . . . . . . 10
4.6. Changes to Internet Facing Servers . . . . . . . . . . . 10
5. Best Current Practices for use of TLS by Mail User Agents . . 10
5.1. Use of SRV records in Establishing Configuration . . . . 12
5.2. Minimum Confidentiality Level . . . . . . . . . . . . . . 13
5.3. Certificiate Validation . . . . . . . . . . . . . . . . . 14
5.4. Certificate Pinning . . . . . . . . . . . . . . . . . . . 14
5.5. Client Certificate Authentication . . . . . . . . . . . . 14
6. Considerations related to Anti-Virus/Anti-Spam Software and
Services . . . . . . . . . . . . . . . . . . . . . . . . . . 15
7. IANA Considerations . . . . . . . . . . . . . . . . . . . . . 15
7.1. POP3S Port Registration Update . . . . . . . . . . . . . 15
7.2. IMAPS Port Registration Update . . . . . . . . . . . . . 16
7.3. Submissions Port Registration . . . . . . . . . . . . . . 16
8. Security Considerations . . . . . . . . . . . . . . . . . . . 17
9. References . . . . . . . . . . . . . . . . . . . . . . . . . 17
9.1. Normative References . . . . . . . . . . . . . . . . . . 17
9.2. Informative References . . . . . . . . . . . . . . . . . 19
Appendix A. Design Considerations . . . . . . . . . . . . . . . 20
Appendix B. Change Log . . . . . . . . . . . . . . . . . . . . . 21
Appendix C. Acknowledgements . . . . . . . . . . . . . . . . . . 26
Authors' Addresses . . . . . . . . . . . . . . . . . . . . . . . 26
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1. Introduction
Software that provides email service via Internet Message Access
Protocol (IMAP) [RFC3501], Post Office Protocol (POP) [RFC1939] and/
or Simple Mail Transfer Protocol (SMTP) Submission [RFC6409] usually
has Transport Layer Security (TLS) [RFC5246] support but often does
not use it in a way that maximizes end-user confidentiality. This
specification describes best current practices for use of TLS in
interactions between Mail User Agents and Mail Access Services, and
between Mail User Agents and Mail Submission Services.
In brief, this memo now recommends that:
o TLS version 1.1 or greater be used for all traffic between mail
user agents (MUAs) and mail submission servers, and also between
MUAs and mail access servers.
o MUAs and mail service providers discourage use of cleartext
protocols for mail access and mail submission, and deprecate use
of cleartext protocols for these purposes as soon as practicable.
o Use of "Implicit TLS" on ports reserved for that purpose, in
preference to STARTTLS on a port that otherwise supports
cleartext.
This memo does not address use of TLS with SMTP for message relay
(where Message Submission [RFC6409] does not apply). Improved use of
TLS with SMTP for message relay requires a different approach. One
approach to address that topic is described in [RFC7672].
The recommendations in this memo do not replace the functionality of,
and are not intended as a substitute for, end-to-end encryption of
electronic mail.
2. Conventions and Terminology Used in This Document
The key words "MUST", "MUST NOT", "REQUIRED", "SHALL", "SHALL NOT",
"SHOULD", "SHOULD NOT", "RECOMMENDED", "MAY", and "OPTIONAL" in this
document are to be interpreted as described in [RFC2119].
The term "Implicit TLS" refers to the automatic negotiation of TLS
whenever a TCP connection is made on a particular TCP port that is
used exclusively by that server for TLS connections. The term
"Implicit TLS" is intended to contrast with use of STARTTLS and
similar commands in POP, IMAP, SMTP message submission, and other
protocols, that are used by client and server to explicitly negotiate
TLS on an established cleartext TCP connection.
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The term "Mail Access Services" includes POP, IMAP and any other
protocol used to access or modify received messages, or to access or
modify a mail user's account configuration.
"Mail Submission Service" refers to the use of the protocol specified
in [RFC6409] (or one of its predecessors or successors) for
submission of outgoing messages for delivery to recipients.
The term "Mail Service Provider" (MSP) refers to a provider of Mail
Access Services and/or Mail Submission Services.
The term "Mail Account" refers to a user's identity with a Mail
Service Provider, that user's authentication credentials, any user
email that is stored by the MSP, and any other per-user configuration
information maintained by the MSP (for example, spam filtering
instructions). Most Mail User Agents (MUAs) support the ability to
access multiple Mail Accounts.
For each account that an MUA accesses on its user's behalf, it must
have the server names, ports, authentication credentials, and other
configuration information specified by the user. This information
which is used by the MUA is referred to as "Mail Account
Configuration"
This specification expresses syntax using the Augmented Backus-Naur
Form (ABNF) as described in [RFC5234], including the core rules in
Appendix B and rules from [RFC5322].
3. Implicit TLS
Previous standards for use of email protocols with TLS used the
STARTTLS mechanism: [RFC2595], [RFC3207], and [RFC3501]. With
STARTTLS, the client establishes a cleartext application session and
determines whether to issue a STARTTLS command based on server
capabilities and client configuration. If the client issues a
STARTTLS command, a TLS handshake follows that can upgrade the
connection. While this mechanism has been deployed, an alternate
mechanism where TLS is negotiated immediately at connection start on
a separate port (referred to in this document as "Implicit TLS") has
been deployed more successfully. To encourage more widespread use of
TLS, and to encourage a greater consistency for how TLS is used, this
specification now recommends use of Implicit TLS for POP, IMAP, SMTP
Submission, and all other protocols used between a Mail User Agent
and a mail service.
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3.1. Implicit TLS for POP
When a TCP connection is established for the "pop3s" service (default
port 995), a TLS handshake begins immediately. Clients MUST
implement the certificate validation mechanism described in
[RFC7817]. Once the TLS session is established, POP3 [RFC1939]
protocol messages are exchanged as TLS application data for the
remainder of the TCP connection. After the server sends a +OK
greeting, the server and client MUST enter AUTHORIZATION state, even
if client credentials were supplied during the TLS handshake.
See Section 5.5 and Section 4.2 for additional information on client
certificate authentication. See Section 7.1 for port registration
information.
3.2. Implicit TLS for IMAP
When a TCP connection is established for the "imaps" service (default
port 993), a TLS handshake begins immediately. Clients MUST
implement the certificate validation mechanism described in [RFC3501]
and SHOULD implement the certificate validation mechanism described
in [RFC7817]. Once the TLS session is established, IMAP [RFC3501]
protocol messages are exchanged as TLS application data for the
remainder of the TCP connection. If client credentials were provided
during the TLS handshake that the server finds acceptable, the server
MAY issue a PREAUTH greeting in which case both the server and client
enter AUTHENTICATED state. If the server issues an OK greeting then
both server and client enter NOT AUTHENTICATED state.
See Section 5.5 and Section 4.2 for additional information on client
certificate authentication. See Section 7.1 for port registration
information. See Section 7.2 for port registration information.
3.3. Implicit TLS for SMTP Submission
When a TCP connection is established for the "submissions" service
(default port 465), a TLS handshake begins immediately. Clients MUST
implement the certificate validation mechanism described in
[RFC7817]. Once a TLS session is established, message submission
protocol data [RFC6409] is exchanged as TLS application data for the
remainder of the TCP connection. (Note: the "submissions" service
name is defined in section 10.3 of this document, and follows the
usual convention that the name of a service layered on top of
Implicit TLS consists of the name of the service as used without TLS,
with an "s" appended.)
The STARTTLS mechanism on port 587 is relatively widely deployed due
to the situation with port 465 (discussed in Section 7.3). This
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differs from IMAP and POP services where Implicit TLS is more widely
deployed on servers than STARTTLS. It is desirable to migrate core
protocols used by MUA software to Implicit TLS over time for
consistency as well as the additional reasons discussed in
Appendix A. However, to maximize use of encryption for submission it
is desirable to support both mechanisms for Message Submission over
TLS for a transition period of several years. As a result, clients
and servers SHOULD implement both STARTTLS on port 587 and Implicit
TLS on port 465 for this transition period. Note that there is no
significant difference between the security properties of STARTTLS on
port 587 and Implicit TLS on port 465 if the implementations are
correct and both client and server are configured to require
successful negotiation of TLS prior to message submission.
Note that the "submissions" port provides access to a Mail Submission
Agent (MSA) as defined in [RFC6409] so requirements and
recommendations for MSAs in that document apply to the submissions
port, including the requirement to implement SMTP AUTH [RFC4954].
See Section 5.5 and Section 4.2 for additional information on client
certificate authentication. See Section 7.3 for port registration
information.
3.4. Implicit TLS Connection Closure for POP, IMAP and SMTP Submission
When a client or server wishes to close the connection, it SHOULD
initiate the exchange of TLS close alerts before TCP connection
termination. The client MAY, after sending a TLS close alert,
gracefully close the TCP connection without waiting for a TLS
response from the server.
4. Best Current Practices for Use of TLS by Mail Access Services and
Message Submission Services
The following practices are recommended for Mail Access Services and
Mail Submission Services:
o Mail Service Providers (MSPs) which support POP, IMAP, and/or
Message Submission, SHOULD provide and support instances of those
services which use Implicit TLS. (See Section 3.)
o For compatibility with existing MUAs and existing MUA
configurations, MSPs SHOULD also, in the near term, provide
instances of these services which support STARTTLS. This will
permit legacy MUAs to discover new availability of TLS capability
on servers, and may increase use of TLS by such MUAs. However,
servers SHOULD NOT advertise STARTTLS if use of the STARTTLS
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command by a client is likely to fail (for example, if the server
has no server certificate configured.)
o MSPs SHOULD advertise their Mail Access Services and Mail
Submission Services using DNS SRV records according to [RFC6186].
Services supporting TLS SHOULD be advertised in preference to
cleartext services (if offered). In addition, services using
Implicit TLS SHOULD be advertised in preference to services
supporting STARTTLS (if offered). (See also Section 4.5.)
o MSPs SHOULD deprecate use of cleartext Mail Access Services and
Mail Submission Services as soon as practicable. (See
Section 4.1.)
o MSPs that provide mail submission as a service, SHOULD support
Mail Submission services using Implicit TLS.
o MSPs currently supporting such use of cleartext SMTP (on port 25)
as a means of message submission by their users (whether or not
requiring authentication) SHOULD transition their users to using
TLS (either Implicit TLS or STARTTLS) as soon as practicable.
o Mail services SHOULD support TLS 1.2 or later.
o All Mail services SHOULD implement the recommended TLS cipher
suites described in [RFC7525] or a future BCP or standards track
revision of that document.
o Mail services currently supporting SSL 2.x, SSL 3.0, or TLS 1.0
SHOULD transition their users to later versions of TLS, and
discontinue support for those versions of SSL and TLS, as soon as
practicable.
o Mail Submission Servers accepting mail using TLS SHOULD include
the TLS ciphersuite of the session in which the mail was received,
in the Received field of the outgoing message. (See Section 4.3.)
o All Mail services implementing TLS SHOULD log TLS cipher
information along with any connection or authentication logs that
they maintain.
Additional considerations and details appear below.
4.1. Deprecation of Services Using Cleartext and TLS Versions < 1.1
The specific means employed for deprecation of cleartext Mail Access
Services and Mail Submission Services this MAY vary from one MSP to
the next in light of their user communities' needs and constraints.
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For example, an MSP MAY implement a gradual transition in which, over
time, more and more users are forbidden to authenticate to cleartext
instances of these services, thus encouraging those users to migrate
to Implicit TLS. Access to cleartext services should eventually be
either disabled, or limited strictly for use by legacy systems which
cannot be upgraded.
After a user's ability to authenticate to a service using cleartext
is revoked, the server denying such access MUST NOT provide any
indication of whether the user's authentication credentials were
valid. An attempt to authenticate as such a user using either
invalid credentials or valid credentials MUST both result in the same
indication of access being denied.
Also, users authenticating with passwords SHOULD be required to
change those passwords when migrating from cleartext to TLS, since
the old passwords were likely to have been compromised.
Transition of users from SSL or TLS 1.0 to later versions of TLS MAY
be accomplished by a means similar to that described above. There
are multiple ways to accomplish this. One way is for the server to
refuse a ClientHello message from any client sending a protocol
version number corresponding to any version of SSL or TLS 1.0.
Another way is for the server to accept ClientHello messages from
some client versions that it does not wish to support, but later
refuse to allow the user to authenticate. The latter method may
provide a better indication to the user of the reason for the failure
but (depending on the protocol and method of authentication used) may
also risk exposure of the user's password over an channel which is
known to not provide adequate confidentiality.
It is RECOMMENDED that new users be required to use TLS version 1.1
or greater from the start. However an MSP may find it necessary to
make exceptions to accommodate some legacy systems which support only
earlier versions of TLS, or only cleartext.
4.2. Mail Server Use of Client Certificate Authentication
Mail servers MAY implement client certificate authentication on the
Implicit TLS port. Servers MUST NOT request a client certificate
during the TLS handshake unless the server is configured to accept
some client certificates as sufficient for authentication and the
server has the ability to determine a mail server authorization
identity matching such certificates. How to make this determination
is presently implementation specific.
If the server accepts the client's certificate as sufficient for
authorization, it MUST enable the SASL EXTERNAL [RFC4422] mechanism.
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An IMAPS server MAY issue a PREAUTH greeting instead of enabling SASL
EXTERNAL.
4.3. Recording TLS Cipher Suite in Received Header
The ESMTPS transmission type [RFC3848] provides trace information
that can indicate TLS was used when transferring mail. However, TLS
usage by itself is not a guarantee of confidentiality or security.
The TLS cipher suite provides additional information about the level
of security made available for a connection. This defines a new SMTP
"tls" Received header additional-registered-clause that is used to
record the TLS cipher suite that was negotiated for the connection.
The value included in this additional clause SHOULD be the registered
cipher suite name (e.g., TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256)
included in the TLS cipher suite registry. In the event the
implementation does not know the name of the cipher suite (a
situation that should be remedied promptly), a four-digit hexadecimal
cipher suite identifier MAY be used. The ABNF for the field follows:
tls-cipher-clause = CFWS "tls" FWS tls-cipher
tls-cipher = tls-cipher-suite-name / tls-cipher-suite-hex
tls-cipher-name = ALPHA *(ALPHA / DIGIT / "_")
; as registered in IANA cipher suite registry
tls-cipher-hex = "0x" 4HEXDIG
4.4. TLS Server Certificate Requirements
MSPs MUST maintain valid server certificates for all servers. See
[RFC7817] for the recommendations and requirements necessary to
achieve this.
If a protocol server provides service for more than one mail domain,
it MAY use a separate IP address for each domain and/or a server
certificate that advertises multiple domains. This will generally be
necessary unless and until it is acceptable to impose the constraint
that the server and all clients support the Server Name Indication
extension to TLS [RFC6066]. For more discussion of this problem, see
section 5.1 of [RFC7817].
4.5. Recommended DNS records for mail protocol servers
This section discusses not only the DNS records that are recommended,
but also implications of DNS records for server configuration and TLS
server certificates.
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4.5.1. MX records
It is recommended that MSPs advertise MX records for handling of
inbound mail (instead of relying entirely on A or AAAA records), and
that those MX records be signed using DNSSEC. This is mentioned here
only for completeness, as handling of inbound mail is out of scope
for this document.
4.5.2. SRV records
MSPs SHOULD advertise SRV records to aid MUAs in determination of
proper configuration of servers, per the instructions in [RFC6186].
MSPs SHOULD advertise servers that support Implicit TLS in preference
to those which support cleartext and/or STARTTLS operation.
4.5.3. DNSSEC
All DNS records advertised by an MSP as a means of aiding clients in
communicating with the MSP's servers, SHOULD be signed using DNSSEC.
4.5.4. TLSA records
MSPs SHOULD advertise TLSA records to provide an additional trust
anchor for public keys used in TLS server certificates. However,
TLSA records MUST NOT be advertised unless they are signed using
DNSSEC.
4.6. Changes to Internet Facing Servers
When an MSP changes the Internet Facing Servers providing mail access
and mail submission services, including SMTP-based spam/virus
filters, it is generally necessary to support the same and/or a newer
version of TLS and the same security directives that were previously
advertised.
5. Best Current Practices for use of TLS by Mail User Agents
It is recommended that Mail User Agents implement the following
practices:
o MUAs SHOULD be capable of using DNS SRV records to discover Mail
Access Services and Mail Submission Services that are advertised
by a MSP for an account being configured. Other means of
discovering server configuration information (e.g. a database
maintained by the MUA vendor) MAY also be supported. (See
Section 5.1 for more information.)
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o MUAs SHOULD be configurable to require a minimum level of
confidentiality for any particular Mail Account, and refuse to
exchange information via any service associated with that Mail
Account if the session does not provide that minimum level of
confidentiality. (See Section 5.2.)
o MUAs MUST NOT consider a session as meeting a minimum level of
confidentiality if the server's TLS certificate cannot be
validated. (See Section 5.3.)
o MUAs MAY impose other minimum confidentiality requirements in the
future, e.g. in order to discourage use of TLS versions or
cryptographic algorithms in which weaknesses have been discovered.
o MUAs SHOULD provide a prominent visual indication of the level of
confidentiality associated with an account configuration (for
example, indications such as "lock" icons or changed background
colors similar to those used by some browsers), at appropriate
times and locations in order to inform the user of the
confidentiality of the communications associated with that
account. For example, this might be done whenever (a) prompting
the user for authentication credentials, (b) the user is composing
mail that will be sent to a particular submission server, (c) a
list of accounts is displayed (particularly if the user can select
from that list to read mail), or (d) the user is requesting to
view or update any configuration data that will be stored on a
remote server.
o MUAs SHOULD implement TLS 1.2 or later. Earlier TLS and SSL
versions MAY also be supported so long as the MUA requires at
least TLS 1.1 when accessing accounts that are configured to
impose minimum confidentiality requirements.
o All MUAs SHOULD implement the recommended TLS cipher suites
described in [RFC7525] or a future BCP or standards track revision
of that document.
o MUAs that are configured to not require minimum confidentiality
for one or more accounts SHOULD detect when TLS becomes available
on those accounts, and offer to upgrade the account to impose
minimum confidentiality requirements.
Additional considerations and details appear below.
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5.1. Use of SRV records in Establishing Configuration
This section updates [RFC6186] by changing the preference rules and
adding a new SRV service label _submissions._tcp to refer to Message
Submission with Implicit TLS.
User-configurable MUAs SHOULD support use of [RFC6186] for account
setup. However, when using configuration information obtained by
this method, MUAs SHOULD ignore advertised services that do not
satisfy minimum confidentiality requirements, unless the user has
explicitly requested reduced confidentiality. This will have the
effect of causing the MUA to default to ignoring advertised
configurations that do not support TLS, even when those advertised
configurations have a higher priority than other advertised
configurations.
When using [RFC6186] configuration information, Mail User Agents
SHOULD NOT automatically establish new configurations that do not
require TLS for all servers, unless there are no advertised
configurations using TLS. If such a configuration is chosen, prior
to attempting to authenticate to the server or use the server for
message submission, the MUA SHOULD warn the user that traffic to that
server will not be encrypted and that it will therefore likely be
intercepted by unauthorized parties. The specific wording is to be
determined by the implementation, but it should adequately capture
the sense of risk given the widespread incidence of mass surveillance
of email traffic.
Similarly, a MUA MUST NOT attempt to "test" a particular mail account
configuration by submitting the user's authentication credentials to
a server, unless a TLS session meeting minimum confidentiality levels
has been established with that server. If minimum confidentiality
requirements have not been satisfied, the MUA must explicitly warn
the user that his password may be exposed to attackers before testing
the new configuration.
When establishing a new configuration for connecting to an IMAP, POP,
or SMTP Submission server, an MUA SHOULD NOT blindly trust SRV
records unless they are signed by DNSSEC and have a valid signature.
Instead, the MUA SHOULD warn the user that the DNS-advertised
mechanism for connecting to the server is not authenticated, and
request the user to manually verify the connection details by
reference to his or her mail service provider's documentation.
Similarly, an MUA MUST NOT consult SRV records to determine which
servers to use on every connection attempt, unless those SRV records
are signed by DNSSEC and have a valid signature. However, an MUA MAY
consult SRV records from time to time to determine if an MSP's server
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configuration has changed, and alert the user if it appears that this
has happened. This can also serve as a means to encourage users to
upgrade their configurations to require TLS if and when their MSPs
support it.
5.2. Minimum Confidentiality Level
MUAs SHOULD, by default, require a minimum level of confidentiality
for services accessed by each account. For MUAs supporting the
ability to access multiple mail accounts, this requirement SHOULD be
configurable on a per-account basis.
The default minimum expected level of confidentiality for all new
accounts SHOULD be at least use of TLS version 1.1 or greater, and
successful validation of the server's certificate. (Future revisions
to this specification may raise these requirements or impose
additional requirements to address newly-discovered weaknesses in
protocols or cryptographic algorithms.)
MUAs MAY permit the user to disable this minimum confidentiality
requirement during initial account configuration, or subsequently
editing an account configuration, but MUST warn users that such a
configuration will not assure privacy for either passwords or
messages.
An MUA which is configured to require a minimum level of
confidentiality for a mail account MUST NOT attempt to perform any
operation other than capability discovery, or STARTTLS for servers
not using Implicit TLS, unless the minimum level of confidentiality
is provided by that connection.
MUAs SHOULD NOT allow users to "click through" to access or send mail
via an connection, or to authenticate to any service using a
password, if that account is configured to impose minimum
confidentiality requirements and that connection does not meet all of
those requirements. Experience indicates that users presented with
such an option often "click through" without understanding the risks
that they're accepting by doing so. Furthermore, users who
frequently find the need to "click through" to use an insecure
connection may become conditioned to do so as a matter of habit,
before considering whether the risks are reasonable in each specific
instance.
An MUA which is not configured to require a minimum level of
confidentiality for a mail account SHOULD still attempt to connect to
the services associated with that account using the most secure means
available, e.g. by using Implicit TLS or STARTTLS.
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5.3. Certificiate Validation
MUAs MUST validate TLS server certificates according to [RFC7817] and
PKIX [RFC5280].
MUAs MAY also support DANE [RFC6698] as a means of validating server
certificates in order to meet minimum confidentiality requirements.
MUAs MAY support use of certificate pinning but MUST NOT consider a
connection in which the server's authenticity relies on certificate
pinning, as providing the minimum level of confidentiality. (See
Section 5.4.)
5.4. Certificate Pinning
During account setup, the MUA will identify servers that provide
account services such as mail access and mail submission (the
previous section describes one way to do this). The certificates for
these servers are verified using the rules described in [RFC7817] and
PKIX [RFC5280]. In the event the certificate does not validate due
to an expired certificate, lack of appropriate chain of trust, or
lack of identifier match, the MUA MAY offer to create a persistent
binding between that certificate and the saved host name for the
server, for use when accessing that account's servers. This is
called certificate pinning.
Certificate pinning is only appropriate during mail account setup and
MUST NOT be offered as an option in response to a failed certificate
validation for an existing mail account. An MUA that allows
certificate pinning MUST NOT allow a certificate pinned for one
account to validate connections for other accounts.
A pinned certificate is subject to a man-in-the-middle attack at
account setup time, and lacks a mechanism to revoke or securely
refresh the certificate. Note also that a man-in-the-middle attack
at account setup time will expose the user's password to the attacker
(if a password is used). Therefore use of a pinned certificate does
not meet the requirement for a minimum confidentiality level, and an
MUA MUST NOT indicate to the user that the such confidentiality is
provided. Additional advice on certificate pinning is present in
[RFC6125].
5.5. Client Certificate Authentication
MUAs MAY implement client certificate authentication on the Implicit
TLS port. An MUA MUST NOT provide a client certificate during the
TLS handshake unless the server requests one and the client has
determined the certificate can be safely used with that specific
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server, OR the client has been explicitly configured by the user to
use that particular certificate with that server. How to make this
determination is presently implementation specific.
A client supporting client certificate authentication with Implicit
TLS MUST implement the SASL EXTERNAL [RFC4422] mechanism using the
appropriate authentication command (AUTH for POP3 [RFC5034], AUTH for
SMTP Submission [RFC4954], AUTHENTICATE for IMAP [RFC3501]).
6. Considerations related to Anti-Virus/Anti-Spam Software and Services
There are multiple ways to connect an Anti-Virus and/or Anti-Spam
(AVAS) service to a mail server. Some mechanisms, such as the de-
facto milter protocol, are out of scope for this specification.
However, some services use an SMTP relay proxy that intercepts mail
at the application layer to perform a scan and proxy or forward to
another MTA. Deploying AVAS services in this way can cause many
problems [RFC2979] including direct interference with this
specification, and other forms of confidentiality or security
reduction. An AVAS product or service is considered compatible with
this specification if all IMAP, POP and SMTP-related software
(including proxies) it includes are compliant with this
specification.
Note that end-to-end email encryption prevents AVAS software and
services from using email content as part of a spam or virus
assessment. Furthermore, while a minimum confidentiality level can
prevent a man-in-the-middle from introducing spam or virus content
between the MUA and Submission server, it does not prevent other
forms of client or account compromise. Use of AVAS services for
submitted email therefore remains necessary.
7. IANA Considerations
7.1. POP3S Port Registration Update
IANA is asked to update the registration of the TCP well-known port
995 using the following template ([RFC6335]):
Service Name: pop3s
Transport Protocol: TCP
Assignee: IETF <iesg@ietf.org>
Contact: IESG <iesg@ietf.org>
Description: POP3 over TLS protocol
Reference: RFC XXXX (this document once published)
Port Number: 995
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7.2. IMAPS Port Registration Update
IANA is asked to update the registration of the TCP well-known port
993 using the following template ([RFC6335]):
Service Name: imaps
Transport Protocol: TCP
Assignee: IETF <iesg@ietf.org>
Contact: IESG <iesg@ietf.org>
Description: IMAP over TLS protocol
Reference: RFC XXXX (this document once published)
Port Number: 993
7.3. Submissions Port Registration
IANA is asked to assign an alternate usage of port 465 in addition to
the current assignment using the following template ([RFC6335]):
Service Name: submissions
Transport Protocol: TCP
Assignee: IETF <iesg@ietf.org>
Contact: IESG <iesg@ietf.org>
Description: Message Submission over TLS protocol
Reference: RFC XXXX (this document once published)
Port Number: 465
This is a one-time procedural exception to the rules in RFC 6335.
This requires explicit IESG approval and does not set a precedent.
Historically, port 465 was briefly registered as the "smtps" port.
This registration made no sense as the SMTP transport MX
infrastructure has no way to specify a port, so port 25 is always
used. As a result, the registration was revoked and was subsequently
reassigned to a different service. In hindsight, the "smtps"
registration should have been renamed or reserved rather than
revoked. Unfortunately, some widely deployed mail software
interpreted "smtps" as "submissions" [RFC6409] and used that port for
email submission by default when an end-user requests security during
account setup. If a new port is assigned for the submissions
service, email software will either continue with unregistered use of
port 465 (leaving the port registry inaccurate relative to de-facto
practice and wasting a well-known port), or confusion between the de-
facto and registered ports will cause harmful interoperability
problems that will deter use of TLS for message submission. The
authors believe both of these outcomes are less desirable than a wart
in the registry documenting real-world usage of a port for two
purposes. Although STARTTLS-on-port-587 has deployed, it has not
replaced deployed use of Implicit TLS submission on port 465.
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8. Security Considerations
This entire document is about security considerations. In general,
this is targeted to improve mail confidentiality and to mitigate
threats external to the email system such as network-level snooping
or interception; this is not intended to mitigate active attackers
who have compromised service provider systems.
It could be argued that sharing the name and version of the client
software with the server has privacy implications. Although
providing this information is not required, it is encouraged so that
mail service providers can more effectively inform end-users running
old clients that they need to upgrade to protect their security, or
know which clients to use in a test deployment prior to upgrading a
server to have higher security requirements.
9. References
9.1. Normative References
[RFC1939] Myers, J. and M. Rose, "Post Office Protocol - Version 3",
STD 53, RFC 1939, DOI 10.17487/RFC1939, May 1996,
<http://www.rfc-editor.org/info/rfc1939>.
[RFC2119] Bradner, S., "Key words for use in RFCs to Indicate
Requirement Levels", BCP 14, RFC 2119,
DOI 10.17487/RFC2119, March 1997,
<http://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, <http://www.rfc-editor.org/info/rfc3207>.
[RFC3501] Crispin, M., "INTERNET MESSAGE ACCESS PROTOCOL - VERSION
4rev1", RFC 3501, DOI 10.17487/RFC3501, March 2003,
<http://www.rfc-editor.org/info/rfc3501>.
[RFC5034] Siemborski, R. and A. Menon-Sen, "The Post Office Protocol
(POP3) Simple Authentication and Security Layer (SASL)
Authentication Mechanism", RFC 5034, DOI 10.17487/RFC5034,
July 2007, <http://www.rfc-editor.org/info/rfc5034>.
[RFC5068] Hutzler, C., Crocker, D., Resnick, P., Allman, E., and T.
Finch, "Email Submission Operations: Access and
Accountability Requirements", BCP 134, RFC 5068,
DOI 10.17487/RFC5068, November 2007,
<http://www.rfc-editor.org/info/rfc5068>.
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[RFC5234] Crocker, D., Ed. and P. Overell, "Augmented BNF for Syntax
Specifications: ABNF", STD 68, RFC 5234,
DOI 10.17487/RFC5234, January 2008,
<http://www.rfc-editor.org/info/rfc5234>.
[RFC5246] Dierks, T. and E. Rescorla, "The Transport Layer Security
(TLS) Protocol Version 1.2", RFC 5246,
DOI 10.17487/RFC5246, August 2008,
<http://www.rfc-editor.org/info/rfc5246>.
[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, DOI 10.17487/RFC5280, May 2008,
<http://www.rfc-editor.org/info/rfc5280>.
[RFC5322] Resnick, P., Ed., "Internet Message Format", RFC 5322,
DOI 10.17487/RFC5322, October 2008,
<http://www.rfc-editor.org/info/rfc5322>.
[RFC6186] Daboo, C., "Use of SRV Records for Locating Email
Submission/Access Services", RFC 6186,
DOI 10.17487/RFC6186, March 2011,
<http://www.rfc-editor.org/info/rfc6186>.
[RFC6409] Gellens, R. and J. Klensin, "Message Submission for Mail",
STD 72, RFC 6409, DOI 10.17487/RFC6409, November 2011,
<http://www.rfc-editor.org/info/rfc6409>.
[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, <http://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,
<http://www.rfc-editor.org/info/rfc7672>.
[RFC7817] Melnikov, A., "Updated Transport Layer Security (TLS)
Server Identity Check Procedure for Email-Related
Protocols", RFC 7817, DOI 10.17487/RFC7817, March 2016,
<http://www.rfc-editor.org/info/rfc7817>.
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9.2. Informative References
[RFC2595] Newman, C., "Using TLS with IMAP, POP3 and ACAP",
RFC 2595, DOI 10.17487/RFC2595, June 1999,
<http://www.rfc-editor.org/info/rfc2595>.
[RFC2979] Freed, N., "Behavior of and Requirements for Internet
Firewalls", RFC 2979, DOI 10.17487/RFC2979, October 2000,
<http://www.rfc-editor.org/info/rfc2979>.
[RFC3848] Newman, C., "ESMTP and LMTP Transmission Types
Registration", RFC 3848, DOI 10.17487/RFC3848, July 2004,
<http://www.rfc-editor.org/info/rfc3848>.
[RFC4422] Melnikov, A., Ed. and K. Zeilenga, Ed., "Simple
Authentication and Security Layer (SASL)", RFC 4422,
DOI 10.17487/RFC4422, June 2006,
<http://www.rfc-editor.org/info/rfc4422>.
[RFC4954] Siemborski, R., Ed. and A. Melnikov, Ed., "SMTP Service
Extension for Authentication", RFC 4954,
DOI 10.17487/RFC4954, July 2007,
<http://www.rfc-editor.org/info/rfc4954>.
[RFC6066] Eastlake 3rd, D., "Transport Layer Security (TLS)
Extensions: Extension Definitions", RFC 6066,
DOI 10.17487/RFC6066, January 2011,
<http://www.rfc-editor.org/info/rfc6066>.
[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, <http://www.rfc-editor.org/info/rfc6125>.
[RFC6335] Cotton, M., Eggert, L., Touch, J., Westerlund, M., and S.
Cheshire, "Internet Assigned Numbers Authority (IANA)
Procedures for the Management of the Service Name and
Transport Protocol Port Number Registry", BCP 165,
RFC 6335, DOI 10.17487/RFC6335, August 2011,
<http://www.rfc-editor.org/info/rfc6335>.
[RFC6698] Hoffman, P. and J. Schlyter, "The DNS-Based Authentication
of Named Entities (DANE) Transport Layer Security (TLS)
Protocol: TLSA", RFC 6698, DOI 10.17487/RFC6698, August
2012, <http://www.rfc-editor.org/info/rfc6698>.
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Appendix A. Design Considerations
This section is not normative.
The first version of this was written independently from draft-moore-
email-tls-00.txt; subsequent versions merge ideas from both drafts.
One author of this document was also the author of RFC 2595 that
became the standard for TLS usage with POP and IMAP, and the other
author was perhaps the first to propose that idea. In hindsight both
authors now believe that that approach was a mistake. At this point
the authors believe that while anything that makes it easier to
deploy TLS is good, the desirable end state is that these protocols
always use TLS, leaving no need for a separate port for cleartext
operation except to support legacy clients while they continue to be
used. The separate port model for TLS is inherently simpler to
implement, debug and deploy. It also enables a "generic TLS load-
balancer" that accepts secure client connections for arbitrary foo-
over-TLS protocols and forwards them to a server that may or may not
support TLS. Such load-balancers cause many problems because they
violate the end-to-end principle and the server loses the ability to
log security-relevant information about the client unless the
protocol is designed to forward that information (as this
specification does for the cipher suite). However, they can result
in TLS deployment where it would not otherwise happen which is a
sufficiently important goal that it overrides the problems.
Although STARTTLS appears only slightly more complex than separate-
port TLS, we again learned the lesson that complexity is the enemy of
security in the form of the STARTTLS command injection vulnerability
(CERT vulnerability ID #555316). Although there's nothing inherently
wrong with STARTTLS, the fact it resulted in a common implementation
error (made independently by multiple implementers) suggests it is a
less secure architecture than Implicit TLS.
Section 7 of RFC 2595 critiques the separate-port approach to TLS.
The first bullet was a correct critique. There are proposals in the
http community to address that, and use of SRV records as described
in RFC 6186 resolves that critique for email. The second bullet is
correct as well, but not very important because useful deployment of
security layers other than TLS in email is small enough to be
effectively irrelevant. The third bullet is incorrect because it
misses the desirable option of "use and latch-on TLS if available".
The fourth bullet may be correct, but is not a problem yet with
current port consumption rates. The fundamental error was
prioritizing a perceived better design based on a mostly valid
critique over real-world deployability. But getting security and
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confidentiality facilities actually deployed is so important it
should trump design purity considerations.
Port 465 is presently used for two purposes: for submissions by a
large number of clients and service providers and for the "urd"
protocol by one vendor. Actually documenting this current state is
controversial as discussed in the IANA considerations section.
However, there is no good alternative. Registering a new port for
submissions when port 465 is widely used for that purpose already
will just create interoperability problems. Registering a port
that's only used if advertised by an SRV record (RFC 6186) would not
create interoperability problems but would require all client and
server deployments and software to change significantly which is
contrary to the goal of promoting more TLS use. Encouraging use of
STARTTLS on port 587 would not create interoperability problems, but
is unlikely to have impact on current undocumented use of port 465
and makes the guidance in this document less consistent. The
remaining option is to document the current state of the world and
support future use of port 465 for submission as this increases
consistency and ease-of-deployment for TLS email submission.
Appendix B. Change Log
Changes since draft-ietf-uta-email-deep-06:
o On the recommendation of one of the co-chairs and some working
group members, rewrote document with the intended status of BCP.
This involved removing a great deal of text that consisted
essentially of new protocol specification, especially the STS
features, on the theory that a BCP should base its recommendations
on current practice, and that new protocol features should be
subject to the interoperability test requirements associated with
normal standards-track documents.
Changes since draft-ietf-uta-email-deep-05:
o Clarify throughout that the confidentiality assurance level
associated with a mail account is a minimum level; attempt to
distinguish this from the current confidentiality level provided
by a connection between client and server.
o Change naming for confidentiality assurance levels: instead of
"high" or "no" confidence, assign numbers 1 and 0 to them
respectively. This because it seems likely that in the not-too-
distant future, what was defined in -05 as "high" confidence will
be considered insufficient, and calling that "high" confidence
will become misleading. For example, relying entirely on a list
of trusted CAs to validate server certificates from arbitrary
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parties, appears to be less and less reliable in practice at
thwarting MITM attacks.
o Clarify that if some services associated with a mail account don't
meet the minimum confidentiality assurance level assigned to that
account, other services that do meet that minimum confidentiality
assurance level may continue to be used.
o Clarify that successful negotiation of at least TLS version 1.1 is
required as a condition of meeting confidentiality assurance level
1.
o Clarify that validation of a server certificate using either DANE
or PKIX is sufficient to meet the certificate validation
requirement of confidentiality assurance level 1.
o Clarify that minimum confidentiality assurance levels are separate
from security directives, and that the requirements of both
mechanisms must be met.
o Explicitly cite an example that a security directive of tls-
version=1.2 won't be saved if the currently negotiated tls-version
is 1.1. (This example already appeared a bit later in the text,
but for author KM it seemed to make the mechanism clearer to use
this example earlier.)
o Clarify some protocol examples as to whether PKIX or DANE was used
to verify a server's certificate.
o Remove most references to DEEP as the conversion from DEEP to MUA-
STS seemed incomplete, but kept the DEEP command for use in POP3
on the assumption that author CN wanted it that way.
o Removed most references to "latch" and derivative words.
o Added pkix+dane as a value for the tls-cert directive, to indicate
(from a server) that both PKIX and DANE validation will be
supported, or (from a client) that both PKIX and DANE were used to
validate a certificate. Also clarified what each of any, pkix,
dane, and pkix+dane mean when advertised by a server and in
particular that tls-cert=any provides no assurance of future PKIX
verifiability in contrast to tls-cert=pkix or tls-cert=pkix+dane.
It seemed important to support the ability to evolve to using
multiple trust anchors for certificate validation, but also to
allow servers to have the option to migrate from PKIX to DANE if
that made sense for them. This change seemed less disruptive than
either defining additional directives, or allowing multiple
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instances of the same directive with different values to appear in
the same advertisement.
o Clarify interaction of this specification with anti-virus / anti-
spam mechanisms.
Changes since draft-ietf-uta-email-deep-04:
o Swap sections 5.1 and 5.3 ("Email Security Tags" and "Server DEEP
Status") as that order may aid understanding of the model. Also
rewrote parts of these two sections to try to make the model
clearer.
o Add text about versioning of security tags to make the model
clearer.
o Add example of security tag upgrade.
o Convert remaining mention of TLS 1.0 to TLS 1.1.
o Change document title from DEEP to MUA STS to align with SMTP
relay STS.
* Slight updates to abstract and introductions.
* Rename security latches/tags to security directives.
* Rename server DEEP status to STS policy.
* Change syntax to use directive-style HSTS syntax.
o Make HSTS reference normative.
o Remove SMTP DSN header as that belongs in SMTP relay STS document.
Changes since draft-ietf-uta-email-deep-03:
o Add more references to ietf-uta-email-tls-certs in implementation
requirements section.
o Replace primary reference to RFC 6125 with ietf-uta-email-tls-
certs, so move RFC 6125 to informative list for this
specification.
Changes since draft-ietf-uta-email-deep-02:
o Make reference to design considerations explicit rather than
"elsewhere in this document".
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o Change provider requirement so SMTP submission services are
separate from SMTP MTA services as opposed to the previous
phrasing that required the servers be separate (which is too
restrictive).
o Update DANE SMTP reference
Changes since draft-ietf-uta-email-deep-01:
o Change text in tls11 and tls12 registrations to clarify
certificate rules, including additional PKIX and DANE references.
o Change from tls10 to tls11 (including reference) as the minimum.
o Fix typo in example 5.
o Remove open issues section; enough time has passed so not worth
waiting for more input.
Changes since draft-ietf-uta-email-deep-00:
o Update and clarify abstract
o use term confidentiality instead of privacy in most cases.
o update open issues to request input for missing text.
o move certificate pinning sub-section to account setup section and
attempt to define it more precisely.
o Add note about end-to-end encryption in AVAS section.
o swap order of DNSSEC and TLSA sub-sections.
o change meaning of 'tls10' and 'tls12' latches to require
certificate validation.
o Replace cipher suite advice with reference to RFC 7525. Change
examples to use TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 as cipher
suite.
o Add text to update IMAP, POP3 and Message Submission standards
with newer TLS advice.
o Add clearer text in introduction that this does not cover SMTP
relay.
o Update references to uta-tls-certs.
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o Add paragraph to Implicit TLS for SMTP Submission section
recommending that STARTTLS also be implemented.
Changes since draft-newman-email-deep-02:
o Changed "privacy assurance" to "confidentiality assurance"
o Changed "low privacy assurance" to "no confidentiality assurance"
o Attempt to improve definition of confidentiality assurance level.
o Add SHOULD indicate when MUA is showing list of mail accounts.
o Add SHOULD NOT latch tls10, tls12 tags until TLS negotiated.
o Removed sentence about deleting and re-creating the account in
latch failure section.
o Remove use of word "fallback" with respect to TLS version
negotiation.
o Added bullet about changes to Internet facing servers to MSP
section.
o minor wording improvements based on feedback
Changes since -01:
o Updated abstract, introduction and document structure to focus
more on mail user agent privacy assurance.
o Added email account privacy section, also moving section on
account setup using SRV records to that section.
o Finished writing IANA considerations section
o Remove provisional concept and instead have server explicitly list
security tags clients should latch.
o Added note that rules for the submissions port follow the same
rules as those for the submit port.
o Reference and update advice in [RFC5068].
o Fixed typo in Client Certificate Authentication section.
o Removed tls-pfs security latch and all mention of perfect forward
secrecy as it was controversial.
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o Added reference to HSTS.
Changes since -00:
o Rewrote introduction to merge ideas from draft-moore-email-tls-00.
o Added Implicit TLS section, Account configuration section and IANA
port registration updates based on draft-moore-email-tls-00.
o Add protocol details necessary to standardize implicit TLS for
POP/IMAP/submission, using ideas from draft-melnikov-pop3-over-
tls.
o Reduce initial set of security tags based on feedback.
o Add deep status concept to allow a window for software updates to
be backed out before latches make that problematic, as well as to
provide service providers with a mechanism they can use to assist
customers in the event of a privacy failure.
o Add DNS SRV section from draft-moore-email-tls-00.
o Write most of the missing IANA considerations section.
o Rewrite most of implementation requirements section based more on
draft-moore-email-tls-00. Remove new cipher requirements for now
because those may be dealt with elsewhere.
Appendix C. Acknowledgements
Thanks to Ned Freed for discussion of the initial latch concepts in
this document. Thanks to Alexey Melnikov for draft-melnikov-pop3-
over-tls-02, which was the basis of the POP3 Implicit TLS text.
Thanks to Russ Housley, Alexey Melnikov and Dan Newman for review
feedback. Thanks to Paul Hoffman for interesting feedback in initial
conversations about this idea.
Authors' Addresses
Keith Moore
Network Heretics
PO Box 1934
Knoxville, TN 37901
US
Email: moore@network-heretics.com
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Chris Newman
Oracle
440 E. Huntington Dr., Suite 400
Arcadia, CA 91006
US
Email: chris.newman@oracle.com
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