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<!DOCTYPE html>
<html lang="en" class="RFC">
<head>
<meta charset="utf-8">
<meta content="Common,Latin" name="scripts">
<meta content="initial-scale=1.0" name="viewport">
<title>RFC 8689: SMTP Require TLS Option</title>
<meta content="Jim Fenton" name="author">
<meta content="
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 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 or by requesting
that recipient-side policy mechanisms such as MTA-STS and DNS-Based
Authentication of Named Entities (DANE) be
ignored when relaying a message for which security is
unimportant.
" name="description">
<meta content="xml2rfc 2.35.0" name="generator">
<meta content="SMTP" name="keyword">
<meta content="8689" name="rfc.number">
<link href="rfc8689.xml" type="application/rfc+xml" rel="alternate">
<link href="#copyright" rel="license">
<style type="text/css">/*
NOTE: Changes at the bottom of this file overrides some earlier settings.
Once the style has stabilized and has been adopted as an official RFC style,
this can be consolidated so that style settings occur only in one place, but
for now the contents of this file consists first of the initial CSS work as
provided to the RFC Formatter (xml2rfc) work, followed by itemized and
commented changes found necssary during the development of the v3
formatters.
*/
/* fonts */
@import url('https://fonts.googleapis.com/css?family=Noto+Sans'); /* Sans-serif */
@import url('https://fonts.googleapis.com/css?family=Noto+Serif'); /* Serif (print) */
@import url('https://fonts.googleapis.com/css?family=Roboto+Mono'); /* Monospace */
@viewport {
zoom: 1.0;
width: extend-to-zoom;
}
@-ms-viewport {
width: extend-to-zoom;
zoom: 1.0;
}
/* general and mobile first */
html {
}
body {
max-width: 90%;
margin: 1.5em auto;
color: #222;
background-color: #fff;
font-size: 14px;
font-family: 'Noto Sans', Arial, Helvetica, sans-serif;
line-height: 1.6;
scroll-behavior: smooth;
}
.ears {
display: none;
}
/* headings */
#title, h1, h2, h3, h4, h5, h6 {
margin: 1em 0 0.5em;
font-weight: bold;
line-height: 1.3;
}
#title {
clear: both;
border-bottom: 1px solid #ddd;
margin: 0 0 0.5em 0;
padding: 1em 0 0.5em;
}
.author {
padding-bottom: 4px;
}
h1 {
font-size: 26px;
margin: 1em 0;
}
h2 {
font-size: 22px;
margin-top: -20px; /* provide offset for in-page anchors */
padding-top: 33px;
}
h3 {
font-size: 18px;
margin-top: -36px; /* provide offset for in-page anchors */
padding-top: 42px;
}
h4 {
font-size: 16px;
margin-top: -36px; /* provide offset for in-page anchors */
padding-top: 42px;
}
h5, h6 {
font-size: 14px;
}
#n-copyright-notice {
border-bottom: 1px solid #ddd;
padding-bottom: 1em;
margin-bottom: 1em;
}
/* general structure */
p {
padding: 0;
margin: 0 0 1em 0;
text-align: left;
}
div, span {
position: relative;
}
div {
margin: 0;
}
.alignRight.art-text {
background-color: #f9f9f9;
border: 1px solid #eee;
border-radius: 3px;
padding: 1em 1em 0;
margin-bottom: 1.5em;
}
.alignRight.art-text pre {
padding: 0;
}
.alignRight {
margin: 1em 0;
}
.alignRight > *:first-child {
border: none;
margin: 0;
float: right;
clear: both;
}
.alignRight > *:nth-child(2) {
clear: both;
display: block;
border: none;
}
svg {
display: block;
}
.alignCenter.art-text {
background-color: #f9f9f9;
border: 1px solid #eee;
border-radius: 3px;
padding: 1em 1em 0;
margin-bottom: 1.5em;
}
.alignCenter.art-text pre {
padding: 0;
}
.alignCenter {
margin: 1em 0;
}
.alignCenter > *:first-child {
border: none;
/* this isn't optimal, but it's an existence proof. PrinceXML doesn't
support flexbox yet.
*/
display: table;
margin: 0 auto;
}
/* lists */
ol, ul {
padding: 0;
margin: 0 0 1em 2em;
}
ol ol, ul ul, ol ul, ul ol {
margin-left: 1em;
}
li {
margin: 0 0 0.25em 0;
}
.ulCompact li {
margin: 0;
}
ul.empty, .ulEmpty {
list-style-type: none;
}
ul.empty li, .ulEmpty li {
margin-top: 0.5em;
}
ul.compact, .ulCompact,
ol.compact, .olCompact {
line-height: 100%;
margin: 0 0 0 2em;
}
/* definition lists */
dl {
}
dl > dt {
float: left;
margin-right: 1em;
}
/*
dl.nohang > dt {
float: none;
}
*/
dl > dd {
margin-bottom: .8em;
min-height: 1.3em;
}
dl.compact > dd, .dlCompact > dd {
margin-bottom: 0em;
}
dl > dd > dl {
margin-top: 0.5em;
margin-bottom: 0em;
}
/* links */
a {
text-decoration: none;
}
a[href] {
color: #22e; /* Arlen: WCAG 2019 */
}
a[href]:hover {
background-color: #f2f2f2;
}
figcaption a[href],
a[href].selfRef {
color: #222;
}
/* XXX probably not this:
a.selfRef:hover {
background-color: transparent;
cursor: default;
} */
/* Figures */
tt, code, pre, code {
background-color: #f9f9f9;
font-family: 'Roboto Mono', monospace;
}
pre {
border: 1px solid #eee;
margin: 0;
padding: 1em;
}
img {
max-width: 100%;
}
figure {
margin: 0;
}
figure blockquote {
margin: 0.8em 0.4em 0.4em;
}
figcaption {
font-style: italic;
margin: 0 0 1em 0;
}
@media screen {
pre {
overflow-x: auto;
max-width: 100%;
max-width: calc(100% - 22px);
}
}
/* aside, blockquote */
aside, blockquote {
margin-left: 0;
padding: 1.2em 2em;
}
blockquote {
background-color: #f9f9f9;
color: #111; /* Arlen: WCAG 2019 */
border: 1px solid #ddd;
border-radius: 3px;
margin: 1em 0;
}
cite {
display: block;
text-align: right;
font-style: italic;
}
/* tables */
table {
width: 100%;
margin: 0 0 1em;
border-collapse: collapse;
border: 1px solid #eee;
}
th, td {
text-align: left;
vertical-align: top;
padding: 0.5em 0.75em;
}
th {
text-align: left;
background-color: #e9e9e9;
}
tr:nth-child(2n+1) > td {
background-color: #f5f5f5;
}
table caption {
font-style: italic;
margin: 0;
padding: 0;
text-align: left;
}
table p {
/* XXX to avoid bottom margin on table row signifiers. If paragraphs should
be allowed within tables more generally, it would be far better to select on a class. */
margin: 0;
}
/* pilcrow */
a.pilcrow {
color: #666; /* Arlen: AHDJ 2019 */
text-decoration: none;
visibility: hidden;
user-select: none;
-ms-user-select: none;
-o-user-select:none;
-moz-user-select: none;
-khtml-user-select: none;
-webkit-user-select: none;
-webkit-touch-callout: none;
}
@media screen {
aside:hover > a.pilcrow,
p:hover > a.pilcrow,
blockquote:hover > a.pilcrow,
div:hover > a.pilcrow,
li:hover > a.pilcrow,
pre:hover > a.pilcrow {
visibility: visible;
}
a.pilcrow:hover {
background-color: transparent;
}
}
/* misc */
hr {
border: 0;
border-top: 1px solid #eee;
}
.bcp14 {
font-variant: small-caps;
}
.role {
font-variant: all-small-caps;
}
/* info block */
#identifiers {
margin: 0;
font-size: 0.9em;
}
#identifiers dt {
width: 3em;
clear: left;
}
#identifiers dd {
float: left;
margin-bottom: 0;
}
#identifiers .authors .author {
display: inline-block;
margin-right: 1.5em;
}
#identifiers .authors .org {
font-style: italic;
}
/* The prepared/rendered info at the very bottom of the page */
.docInfo {
color: #666; /* Arlen: WCAG 2019 */
font-size: 0.9em;
font-style: italic;
margin-top: 2em;
}
.docInfo .prepared {
float: left;
}
.docInfo .prepared {
float: right;
}
/* table of contents */
#toc {
padding: 0.75em 0 2em 0;
margin-bottom: 1em;
}
nav.toc ul {
margin: 0 0.5em 0 0;
padding: 0;
list-style: none;
}
nav.toc li {
line-height: 1.3em;
margin: 0.75em 0;
padding-left: 1.2em;
text-indent: -1.2em;
}
/* references */
.references dt {
text-align: right;
font-weight: bold;
min-width: 7em;
}
.references dd {
margin-left: 8em;
overflow: auto;
}
.refInstance {
margin-bottom: 1.25em;
}
.references .ascii {
margin-bottom: 0.25em;
}
/* index */
.index ul {
margin: 0 0 0 1em;
padding: 0;
list-style: none;
}
.index ul ul {
margin: 0;
}
.index li {
margin: 0;
text-indent: -2em;
padding-left: 2em;
padding-bottom: 5px;
}
.indexIndex {
margin: 0.5em 0 1em;
}
.index a {
font-weight: 700;
}
/* make the index two-column on all but the smallest screens */
@media (min-width: 600px) {
.index ul {
-moz-column-count: 2;
-moz-column-gap: 20px;
}
.index ul ul {
-moz-column-count: 1;
-moz-column-gap: 0;
}
}
/* authors */
address.vcard {
font-style: normal;
margin: 1em 0;
}
address.vcard .nameRole {
font-weight: 700;
margin-left: 0;
}
address.vcard .label {
font-family: "Noto Sans",Arial,Helvetica,sans-serif;
margin: 0.5em 0;
}
address.vcard .type {
display: none;
}
.alternative-contact {
margin: 1.5em 0 1em;
}
hr.addr {
border-top: 1px dashed;
margin: 0;
color: #ddd;
max-width: calc(100% - 16px);
}
/* temporary notes */
.rfcEditorRemove::before {
position: absolute;
top: 0.2em;
right: 0.2em;
padding: 0.2em;
content: "The RFC Editor will remove this note";
color: #9e2a00; /* Arlen: WCAG 2019 */
background-color: #ffd; /* Arlen: WCAG 2019 */
}
.rfcEditorRemove {
position: relative;
padding-top: 1.8em;
background-color: #ffd; /* Arlen: WCAG 2019 */
border-radius: 3px;
}
.cref {
background-color: #ffd; /* Arlen: WCAG 2019 */
padding: 2px 4px;
}
.crefSource {
font-style: italic;
}
/* alternative layout for smaller screens */
@media screen and (max-width: 1023px) {
body {
padding-top: 2em;
}
#title {
padding: 1em 0;
}
h1 {
font-size: 24px;
}
h2 {
font-size: 20px;
margin-top: -18px; /* provide offset for in-page anchors */
padding-top: 38px;
}
#identifiers dd {
max-width: 60%;
}
#toc {
position: fixed;
z-index: 2;
top: 0;
right: 0;
padding: 0;
margin: 0;
background-color: inherit;
border-bottom: 1px solid #ccc;
}
#toc h2 {
margin: -1px 0 0 0;
padding: 4px 0 4px 6px;
padding-right: 1em;
min-width: 190px;
font-size: 1.1em;
text-align: right;
background-color: #444;
color: white;
cursor: pointer;
}
#toc h2::before { /* css hamburger */
float: right;
position: relative;
width: 1em;
height: 1px;
left: -164px;
margin: 6px 0 0 0;
background: white none repeat scroll 0 0;
box-shadow: 0 4px 0 0 white, 0 8px 0 0 white;
content: "";
}
#toc nav {
display: none;
padding: 0.5em 1em 1em;
overflow: auto;
height: calc(100vh - 48px);
border-left: 1px solid #ddd;
}
}
/* alternative layout for wide screens */
@media screen and (min-width: 1024px) {
body {
max-width: 724px;
margin: 42px auto;
padding-left: 1.5em;
padding-right: 29em;
}
#toc {
position: fixed;
top: 42px;
right: 42px;
width: 25%;
margin: 0;
padding: 0 1em;
z-index: 1;
}
#toc h2 {
border-top: none;
border-bottom: 1px solid #ddd;
font-size: 1em;
font-weight: normal;
margin: 0;
padding: 0.25em 1em 1em 0;
}
#toc nav {
display: block;
height: calc(90vh - 84px);
bottom: 0;
padding: 0.5em 0 0;
overflow: auto;
}
img { /* future proofing */
max-width: 100%;
height: auto;
}
}
/* pagination */
@media print {
body {
width: 100%;
}
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<link href="https://dx.doi.org/10.17487/rfc8689" rel="alternate">
<link href="urn:issn:2070-1721" rel="alternate">
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<table class="ears">
<thead><tr>
<td class="left">RFC 8689</td>
<td class="center">SMTP Require TLS Option</td>
<td class="right">November 2019</td>
</tr></thead>
<tfoot><tr>
<td class="left">Fenton</td>
<td class="center">Standards Track</td>
<td class="right">[Page]</td>
</tr></tfoot>
</table>
<div id="external-metadata" class="document-information"></div>
<div id="internal-metadata" class="document-information">
<dl id="identifiers">
<dt class="label-stream">Stream:</dt>
<dd class="stream">Internet Engineering Task Force (IETF)</dd>
<dt class="label-rfc">RFC:</dt>
<dd class="rfc"><a href="https://www.rfc-editor.org/rfc/rfc8689" class="eref">8689</a></dd>
<dt class="label-category">Category:</dt>
<dd class="category">Standards Track</dd>
<dt class="label-published">Published:</dt>
<dd class="published">
<time datetime="2019-11" class="published">November 2019</time>
</dd>
<dt class="label-issn">ISSN:</dt>
<dd class="issn">2070-1721</dd>
<dt class="label-authors">Author:</dt>
<dd class="authors">
<div class="author">
<div class="author-name">J. Fenton</div>
<div class="org">Altmode Networks</div>
</div>
</dd>
</dl>
</div>
<h1 id="rfcnum">RFC 8689</h1>
<h1 id="title">SMTP Require TLS Option</h1>
<section id="section-abstract">
<h2 id="abstract"><a href="#abstract" class="selfRef">Abstract</a></h2>
<p id="section-abstract-1">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 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 or by requesting
that recipient-side policy mechanisms such as MTA-STS and DNS-Based
Authentication of Named Entities (DANE) be
ignored when relaying a message for which security is
unimportant.<a href="#section-abstract-1" class="pilcrow">¶</a></p>
</section>
<div id="status-of-memo">
<section id="section-boilerplate.1">
<h2 id="name-status-of-this-memo">
<a href="#name-status-of-this-memo" class="section-name selfRef">Status of This Memo</a>
</h2>
<p id="section-boilerplate.1-1">
This is an Internet Standards Track document.<a href="#section-boilerplate.1-1" class="pilcrow">¶</a></p>
<p id="section-boilerplate.1-2">
This document is a product of the Internet Engineering Task Force
(IETF). It represents the consensus of the IETF community. It has
received public review and has been approved for publication by
the Internet Engineering Steering Group (IESG). Further
information on Internet Standards is available in Section 2 of
RFC 7841.<a href="#section-boilerplate.1-2" class="pilcrow">¶</a></p>
<p id="section-boilerplate.1-3">
Information about the current status of this document, any
errata, and how to provide feedback on it may be obtained at
<span><a href="https://www.rfc-editor.org/info/rfc8689">https://www.rfc-editor.org/info/rfc8689</a></span>.<a href="#section-boilerplate.1-3" class="pilcrow">¶</a></p>
</section>
</div>
<div id="copyright">
<section id="section-boilerplate.2">
<h2 id="name-copyright-notice">
<a href="#name-copyright-notice" class="section-name selfRef">Copyright Notice</a>
</h2>
<p id="section-boilerplate.2-1">
Copyright (c) 2019 IETF Trust and the persons identified as the
document authors. All rights reserved.<a href="#section-boilerplate.2-1" class="pilcrow">¶</a></p>
<p id="section-boilerplate.2-2">
This document is subject to BCP 78 and the IETF Trust's Legal
Provisions Relating to IETF Documents
(<span><a href="https://trustee.ietf.org/license-info">https://trustee.ietf.org/license-info</a></span>) 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 the Trust Legal Provisions and are provided without
warranty as described in the Simplified BSD License.<a href="#section-boilerplate.2-2" class="pilcrow">¶</a></p>
</section>
</div>
<div id="toc">
<section id="section-toc.1">
<a href="#" onclick="scroll(0,0)" class="toplink">▲</a><h2 id="name-table-of-contents">
<a href="#name-table-of-contents" class="section-name selfRef">Table of Contents</a>
</h2>
<nav class="toc"><ul class="toc ulEmpty">
<li class="toc ulEmpty" id="section-toc.1-1.1">
<p id="section-toc.1-1.1.1"><a href="#section-1" class="xref">1</a>. <a href="#name-introduction" class="xref">Introduction</a><a href="#section-toc.1-1.1.1" class="pilcrow">¶</a></p>
<ul class="toc ulEmpty">
<li class="toc ulEmpty" id="section-toc.1-1.1.2.1">
<p id="section-toc.1-1.1.2.1.1"><a href="#section-1.1" class="xref">1.1</a>. <a href="#name-requirements-language" class="xref">Requirements Language</a><a href="#section-toc.1-1.1.2.1.1" class="pilcrow">¶</a></p>
</li>
</ul>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.2">
<p id="section-toc.1-1.2.1"><a href="#section-2" class="xref">2</a>. <a href="#name-the-requiretls-service-exte" class="xref">The REQUIRETLS Service Extension</a><a href="#section-toc.1-1.2.1" class="pilcrow">¶</a></p>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.3">
<p id="section-toc.1-1.3.1"><a href="#section-3" class="xref">3</a>. <a href="#name-the-tls-required-header-fie" class="xref">The TLS-Required Header Field</a><a href="#section-toc.1-1.3.1" class="pilcrow">¶</a></p>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.4">
<p id="section-toc.1-1.4.1"><a href="#section-4" class="xref">4</a>. <a href="#name-requiretls-semantics" class="xref">REQUIRETLS Semantics</a><a href="#section-toc.1-1.4.1" class="pilcrow">¶</a></p>
<ul class="toc ulEmpty">
<li class="toc ulEmpty" id="section-toc.1-1.4.2.1">
<p id="section-toc.1-1.4.2.1.1"><a href="#section-4.1" class="xref">4.1</a>. <a href="#name-requiretls-receipt-requirem" class="xref">REQUIRETLS Receipt Requirements</a><a href="#section-toc.1-1.4.2.1.1" class="pilcrow">¶</a></p>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.4.2.2">
<p id="section-toc.1-1.4.2.2.1"><a href="#section-4.2" class="xref">4.2</a>. <a href="#name-requiretls-sender-requireme" class="xref">REQUIRETLS Sender Requirements</a><a href="#section-toc.1-1.4.2.2.1" class="pilcrow">¶</a></p>
<ul class="toc ulEmpty">
<li class="toc ulEmpty" id="section-toc.1-1.4.2.2.2.1">
<p id="section-toc.1-1.4.2.2.2.1.1"><a href="#section-4.2.1" class="xref">4.2.1</a>. <a href="#name-sending-with-tls-required" class="xref">Sending with TLS Required</a><a href="#section-toc.1-1.4.2.2.2.1.1" class="pilcrow">¶</a></p>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.4.2.2.2.2">
<p id="section-toc.1-1.4.2.2.2.2.1"><a href="#section-4.2.2" class="xref">4.2.2</a>. <a href="#name-sending-with-tls-optional" class="xref">Sending with TLS Optional</a><a href="#section-toc.1-1.4.2.2.2.2.1" class="pilcrow">¶</a></p>
</li>
</ul>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.4.2.3">
<p id="section-toc.1-1.4.2.3.1"><a href="#section-4.3" class="xref">4.3</a>. <a href="#name-requiretls-submission" class="xref">REQUIRETLS Submission</a><a href="#section-toc.1-1.4.2.3.1" class="pilcrow">¶</a></p>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.4.2.4">
<p id="section-toc.1-1.4.2.4.1"><a href="#section-4.4" class="xref">4.4</a>. <a href="#name-delivery-of-requiretls-mess" class="xref">Delivery of REQUIRETLS messages</a><a href="#section-toc.1-1.4.2.4.1" class="pilcrow">¶</a></p>
</li>
</ul>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.5">
<p id="section-toc.1-1.5.1"><a href="#section-5" class="xref">5</a>. <a href="#name-non-delivery-message-handli" class="xref">Non-delivery Message Handling</a><a href="#section-toc.1-1.5.1" class="pilcrow">¶</a></p>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.6">
<p id="section-toc.1-1.6.1"><a href="#section-6" class="xref">6</a>. <a href="#name-reorigination-consideration" class="xref">Reorigination Considerations</a><a href="#section-toc.1-1.6.1" class="pilcrow">¶</a></p>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.7">
<p id="section-toc.1-1.7.1"><a href="#section-7" class="xref">7</a>. <a href="#name-iana-considerations" class="xref">IANA Considerations</a><a href="#section-toc.1-1.7.1" class="pilcrow">¶</a></p>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.8">
<p id="section-toc.1-1.8.1"><a href="#section-8" class="xref">8</a>. <a href="#name-security-considerations" class="xref">Security Considerations</a><a href="#section-toc.1-1.8.1" class="pilcrow">¶</a></p>
<ul class="toc ulEmpty">
<li class="toc ulEmpty" id="section-toc.1-1.8.2.1">
<p id="section-toc.1-1.8.2.1.1"><a href="#section-8.1" class="xref">8.1</a>. <a href="#name-passive-attacks" class="xref">Passive Attacks</a><a href="#section-toc.1-1.8.2.1.1" class="pilcrow">¶</a></p>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.8.2.2">
<p id="section-toc.1-1.8.2.2.1"><a href="#section-8.2" class="xref">8.2</a>. <a href="#name-active-attacks" class="xref">Active Attacks</a><a href="#section-toc.1-1.8.2.2.1" class="pilcrow">¶</a></p>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.8.2.3">
<p id="section-toc.1-1.8.2.3.1"><a href="#section-8.3" class="xref">8.3</a>. <a href="#name-bad-actor-mtas" class="xref">Bad-Actor MTAs</a><a href="#section-toc.1-1.8.2.3.1" class="pilcrow">¶</a></p>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.8.2.4">
<p id="section-toc.1-1.8.2.4.1"><a href="#section-8.4" class="xref">8.4</a>. <a href="#name-policy-conflicts" class="xref">Policy Conflicts</a><a href="#section-toc.1-1.8.2.4.1" class="pilcrow">¶</a></p>
</li>
</ul>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.9">
<p id="section-toc.1-1.9.1"><a href="#section-9" class="xref">9</a>. <a href="#name-references" class="xref">References</a><a href="#section-toc.1-1.9.1" class="pilcrow">¶</a></p>
<ul class="toc ulEmpty">
<li class="toc ulEmpty" id="section-toc.1-1.9.2.1">
<p id="section-toc.1-1.9.2.1.1"><a href="#section-9.1" class="xref">9.1</a>. <a href="#name-normative-references" class="xref">Normative References</a><a href="#section-toc.1-1.9.2.1.1" class="pilcrow">¶</a></p>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.9.2.2">
<p id="section-toc.1-1.9.2.2.1"><a href="#section-9.2" class="xref">9.2</a>. <a href="#name-informative-references" class="xref">Informative References</a><a href="#section-toc.1-1.9.2.2.1" class="pilcrow">¶</a></p>
</li>
</ul>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.10">
<p id="section-toc.1-1.10.1"><a href="#section-appendix.a" class="xref">Appendix A</a>. <a href="#name-examples" class="xref">Examples</a><a href="#section-toc.1-1.10.1" class="pilcrow">¶</a></p>
<ul class="toc ulEmpty">
<li class="toc ulEmpty" id="section-toc.1-1.10.2.1">
<p id="section-toc.1-1.10.2.1.1"><a href="#section-a.1" class="xref">A.1</a>. <a href="#name-requiretls-smtp-option" class="xref">REQUIRETLS SMTP Option</a><a href="#section-toc.1-1.10.2.1.1" class="pilcrow">¶</a></p>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.10.2.2">
<p id="section-toc.1-1.10.2.2.1"><a href="#section-a.2" class="xref">A.2</a>. <a href="#name-tls-required-header-field" class="xref">TLS-Required Header Field</a><a href="#section-toc.1-1.10.2.2.1" class="pilcrow">¶</a></p>
</li>
</ul>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.11">
<p id="section-toc.1-1.11.1"><a href="#section-appendix.b" class="xref"></a><a href="#name-acknowledgements" class="xref">Acknowledgements</a><a href="#section-toc.1-1.11.1" class="pilcrow">¶</a></p>
</li>
<li class="toc ulEmpty" id="section-toc.1-1.12">
<p id="section-toc.1-1.12.1"><a href="#section-appendix.c" class="xref"></a><a href="#name-authors-address" class="xref">Author's Address</a><a href="#section-toc.1-1.12.1" class="pilcrow">¶</a></p>
</li>
</ul>
</nav>
</section>
</div>
<section id="section-1">
<h2 id="name-introduction">
<a href="#section-1" class="section-number selfRef">1. </a><a href="#name-introduction" class="section-name selfRef">Introduction</a>
</h2>
<p id="section-1-1">The <span><a href="#RFC5321" class="xref">SMTP</a> [<a href="#RFC5321" class="xref">RFC5321</a>]</span> <span><a href="#RFC3207" class="xref">STARTTLS service extension</a> [<a href="#RFC3207" class="xref">RFC3207</a>]</span> 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.<a href="#section-1-1" class="pilcrow">¶</a></p>
<p id="section-1-2">Policy mechanisms such as <span><a href="#RFC7672" class="xref">DANE</a> [<a href="#RFC7672" class="xref">RFC7672</a>]</span>
and <span><a href="#RFC8461" class="xref">MTA-STS</a> [<a href="#RFC8461" class="xref">RFC8461</a>]</span> 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 and which ones are less sensitive and
ought to be relayed even if TLS cannot be negotiated
successfully.<a href="#section-1-2" class="pilcrow">¶</a></p>
<p id="section-1-3">The default opportunistic nature of SMTP TLS enables several
on-the-wire attacks on SMTP security between MTAs. These
include passive eavesdropping on connections for which TLS 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 <a href="#Security" class="xref">Security Considerations</a> section
of this
document.<a href="#section-1-3" class="pilcrow">¶</a></p>
<p id="section-1-4">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
<span class="bcp14">MUST</span> 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.<a href="#section-1-4" class="pilcrow">¶</a></p>
<p id="section-1-5">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.<a href="#section-1-5" class="pilcrow">¶</a></p>
<section id="section-1.1">
<h3 id="name-requirements-language">
<a href="#section-1.1" class="section-number selfRef">1.1. </a><a href="#name-requirements-language" class="section-name selfRef">Requirements Language</a>
</h3>
<p id="section-1.1-1">
The key words "<span class="bcp14">MUST</span>", "<span class="bcp14">MUST NOT</span>",
"<span class="bcp14">REQUIRED</span>", "<span class="bcp14">SHALL</span>", "<span class="bcp14">SHALL NOT</span>", "<span class="bcp14">SHOULD</span>", "<span class="bcp14">SHOULD NOT</span>",
"<span class="bcp14">RECOMMENDED</span>", "<span class="bcp14">NOT RECOMMENDED</span>",
"<span class="bcp14">MAY</span>", and "<span class="bcp14">OPTIONAL</span>" in this document are
to be interpreted as described in BCP 14 <span>[<a href="#RFC2119" class="xref">RFC2119</a>]</span>
<span>[<a href="#RFC8174" class="xref">RFC8174</a>]</span> when, and only when, they appear in all capitals,
as shown here.<a href="#section-1.1-1" class="pilcrow">¶</a></p>
<p id="section-1.1-2">The formal syntax uses the Augmented Backus-Naur Form (ABNF)
<span>[<a href="#RFC5234" class="xref">RFC5234</a>]</span>, including the core rules defined in
Appendix B of that document.<a href="#section-1.1-2" class="pilcrow">¶</a></p>
</section>
</section>
<div id="service_extension">
<section id="section-2">
<h2 id="name-the-requiretls-service-exte">
<a href="#section-2" class="section-number selfRef">2. </a><a href="#name-the-requiretls-service-exte" class="section-name selfRef">The REQUIRETLS Service Extension</a>
</h2>
<p id="section-2-1">The REQUIRETLS SMTP service extension has the following characteristics:<a href="#section-2-1" class="pilcrow">¶</a></p>
<ol start="1" type="1" class="normal" id="section-2-2">
<li id="section-2-2.1">The textual name of the extension is "Require TLS".<a href="#section-2-2.1" class="pilcrow">¶</a>
</li>
<li id="section-2-2.2">The EHLO keyword value associated with this extension is
"REQUIRETLS".<a href="#section-2-2.2" class="pilcrow">¶</a>
</li>
<li id="section-2-2.3">No additional SMTP verbs are defined by this extension.<a href="#section-2-2.3" class="pilcrow">¶</a>
</li>
<li id="section-2-2.4">One optional parameter ("REQUIRETLS") is added to the MAIL
FROM command by this extension. No value is associated with
this parameter.<a href="#section-2-2.4" class="pilcrow">¶</a>
</li>
<li id="section-2-2.5">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.<a href="#section-2-2.5" class="pilcrow">¶</a>
</li>
<li id="section-2-2.6">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 support
the REQUIRETLS extension.<a href="#section-2-2.6" class="pilcrow">¶</a>
</li>
<li id="section-2-2.7">The REQUIRETLS extension is valid for message relay <span>[<a href="#RFC5321" class="xref">RFC5321</a>]</span>, submission <span>[<a href="#RFC6409" class="xref">RFC6409</a>]</span>, and the Local Mail Transfer Protocol
(LMTP) <span>[<a href="#RFC2033" class="xref">RFC2033</a>]</span>.<a href="#section-2-2.7" class="pilcrow">¶</a>
</li>
<li id="section-2-2.8">
<p id="section-2-2.8.1">The ABNF syntax for the MAIL FROM parameter is as follows:<a href="#section-2-2.8.1" class="pilcrow">¶</a></p>
<div id="section-2-2.8.2">
<pre class="sourcecode lang-abnf">
requiretls-param = "REQUIRETLS"
; where requiretls-param is an instance of an
; esmtp-param used in Mail-parameters in
; RFC 5321, Section 4.1.2. There is no esmtp-value
; associated with requiretls-param. </pre><a href="#section-2-2.8.2" class="pilcrow">¶</a>
</div>
</li>
</ol>
<p id="section-2-3">In order to specify REQUIRETLS treatment for a given message,
the REQUIRETLS option is specified in the MAIL FROM command when
that message is transmitted. This option <span class="bcp14">MUST</span> only be specified in the
context of an SMTP session meeting the security requirements of
REQUIRETLS:<a href="#section-2-3" class="pilcrow">¶</a></p>
<ul>
<li id="section-2-4.1">The session itself <span class="bcp14">MUST</span> employ TLS transmission.<a href="#section-2-4.1" class="pilcrow">¶</a>
</li>
<li id="section-2-4.2">If the SMTP server to which the message is being transmitted
is identified through an MX record lookup, its name
<span class="bcp14">MUST</span> be validated via a DNSSEC signature on the recipient
domain's MX record, or the MX hostname <span class="bcp14">MUST</span> be
validated by an MTA-STS policy as described in <span><a href="https://www.rfc-editor.org/rfc/rfc8461#section-4.1" class="relref">Section 4.1</a> of [<a href="#RFC8461" class="xref">RFC8461</a>]</span>. DNSSEC is defined
in <span>[<a href="#RFC4033" class="xref">RFC4033</a>]</span>,
<span>[<a href="#RFC4034" class="xref">RFC4034</a>]</span>, and
<span>[<a href="#RFC4035" class="xref">RFC4035</a>]</span>.<a href="#section-2-4.2" class="pilcrow">¶</a>
</li>
<li id="section-2-4.3">The certificate presented by the SMTP server either <span class="bcp14">MUST</span>
be verified successfully by a trust chain leading to a certificate
trusted by the SMTP client, or it <span class="bcp14">MUST</span> be verified successfully using
DANE, as specified in <span>[<a href="#RFC7672" class="xref">RFC7672</a>]</span>. For trust chains, the
choice of trusted (root) certificates is at the discretion of
the SMTP client.<a href="#section-2-4.3" class="pilcrow">¶</a>
</li>
<li id="section-2-4.4">Following the negotiation of STARTTLS, the SMTP server <span class="bcp14">MUST</span>
advertise in the subsequent EHLO response that it supports REQUIRETLS.<a href="#section-2-4.4" class="pilcrow">¶</a>
</li>
</ul>
</section>
</div>
<div id="header_field">
<section id="section-3">
<h2 id="name-the-tls-required-header-fie">
<a href="#section-3" class="section-number selfRef">3. </a><a href="#name-the-tls-required-header-fie" class="section-name selfRef">The TLS-Required Header Field</a>
</h2>
<p id="section-3-1">One new message header field <span>[<a href="#RFC5322" class="xref">RFC5322</a>]</span>,
TLS-Required, is defined by this
specification. It is used for messages for which the originator
requests that the recipient
TLS policy (including <span><a href="#RFC8461" class="xref">MTA-STS</a> [<a href="#RFC8461" class="xref">RFC8461</a>]</span> and
<span><a href="#RFC7672" class="xref">DANE</a> [<a href="#RFC7672" class="xref">RFC7672</a>]</span>) be ignored. This might be
done, for example, to report a misconfigured mail server, such as
an expired TLS certificate.<a href="#section-3-1" class="pilcrow">¶</a></p>
<p id="section-3-2">The TLS-Required header field has a single <span class="bcp14">REQUIRED</span> parameter:<a href="#section-3-2" class="pilcrow">¶</a></p>
<ul>
<li id="section-3-3.1">No - The SMTP client <span class="bcp14">SHOULD</span> 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 <span class="bcp14">SHOULD</span> negotiate
STARTTLS with the server if available.<a href="#section-3-3.1" class="pilcrow">¶</a>
</li>
</ul>
<p id="section-3-4">More than one instance of the TLS-Required header field <span class="bcp14">MUST NOT</span> appear in a given message.<a href="#section-3-4" class="pilcrow">¶</a></p>
<p id="section-3-5">The ABNF syntax for the TLS-Required header field is as
follows:<a href="#section-3-5" class="pilcrow">¶</a></p>
<div id="section-3-6">
<pre class="sourcecode lang-abnf">
requiretls-field = "TLS-Required:" [FWS] "No" CRLF
; where requiretls-field in an instance of an
; optional-field defined in RFC 5322, Section 3.6.8.
FWS = <as defined in RFC 5322>
CRLF = <as defined in RFC 5234> </pre><a href="#section-3-6" class="pilcrow">¶</a>
</div>
</section>
</div>
<div id="semantics">
<section id="section-4">
<h2 id="name-requiretls-semantics">
<a href="#section-4" class="section-number selfRef">4. </a><a href="#name-requiretls-semantics" class="section-name selfRef">REQUIRETLS Semantics</a>
</h2>
<div id="receipt">
<section id="section-4.1">
<h3 id="name-requiretls-receipt-requirem">
<a href="#section-4.1" class="section-number selfRef">4.1. </a><a href="#name-requiretls-receipt-requirem" class="section-name selfRef">REQUIRETLS Receipt Requirements</a>
</h3>
<p id="section-4.1-1">Upon receipt of the REQUIRETLS option on a MAIL FROM command
during the receipt of a message, an SMTP server <span class="bcp14">MUST</span> tag that
message as needing REQUIRETLS handling.<a href="#section-4.1-1" class="pilcrow">¶</a></p>
<p id="section-4.1-2">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 <span class="bcp14">MUST</span> 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
<span class="bcp14">MUST</span> be ignored but <span class="bcp14">MAY</span> be included in the onward relay of the
message.<a href="#section-4.1-2" class="pilcrow">¶</a></p>
<p id="section-4.1-3">The manner in which the above tagging takes place is
implementation dependent. If the message is being locally
aliased and redistributed to multiple addresses, all instances
of the message <span class="bcp14">MUST</span> be tagged in the same manner.<a href="#section-4.1-3" class="pilcrow">¶</a></p>
</section>
</div>
<div id="sender">
<section id="section-4.2">
<h3 id="name-requiretls-sender-requireme">
<a href="#section-4.2" class="section-number selfRef">4.2. </a><a href="#name-requiretls-sender-requireme" class="section-name selfRef">REQUIRETLS Sender Requirements</a>
</h3>
<div id="yestls">
<section id="section-4.2.1">
<h4 id="name-sending-with-tls-required">
<a href="#section-4.2.1" class="section-number selfRef">4.2.1. </a><a href="#name-sending-with-tls-required" class="section-name selfRef">Sending with TLS Required</a>
</h4>
<p id="section-4.2.1-1">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 <span class="bcp14">MUST</span>:<a href="#section-4.2.1-1" class="pilcrow">¶</a></p>
<ol start="1" type="1" class="normal" id="section-4.2.1-2">
<li id="section-4.2.1-2.1">Look up the SMTP server to which the message is to be sent,
as described in <span>[<a href="#RFC5321" class="xref">RFC5321</a>], <a href="https://www.rfc-editor.org/rfc/rfc5321#section-5.1" class="relref">Section 5.1</a></span>.<a href="#section-4.2.1-2.1" class="pilcrow">¶</a>
</li>
<li id="section-4.2.1-2.2">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 <span class="bcp14">MUST</span> also validate the SMTP
server name using MTA-STS, as described in
<span>[<a href="#RFC8461" class="xref">RFC8461</a>], <a href="https://www.rfc-editor.org/rfc/rfc8461#section-4.1" class="relref">Section 4.1</a></span>.<a href="#section-4.2.1-2.2" class="pilcrow">¶</a>
</li>
<li id="section-4.2.1-2.3">Open an SMTP session with the peer SMTP server using the
EHLO verb.<a href="#section-4.2.1-2.3" class="pilcrow">¶</a>
</li>
<li id="section-4.2.1-2.4">Establish a TLS-protected SMTP session with its peer SMTP
server and authenticate the server's certificate as specified
in <span>[<a href="#RFC6125" class="xref">RFC6125</a>]</span> or <span>[<a href="#RFC7672" class="xref">RFC7672</a>]</span>, 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) <span class="bcp14">MUST</span> match the DNS-ID
or CN-ID of the certificate presented by the server.<a href="#section-4.2.1-2.4" class="pilcrow">¶</a>
</li>
<li id="section-4.2.1-2.5">Ensure that the response to the subsequent EHLO following
establishment of the TLS protection advertises the REQUIRETLS
capability.<a href="#section-4.2.1-2.5" class="pilcrow">¶</a>
</li>
</ol>
<p id="section-4.2.1-3">The SMTP client <span class="bcp14">SHOULD</span> follow the recommendations in <span>[<a href="#RFC7525" class="xref">RFC7525</a>]</span> or its successor with respect to
negotiation of the TLS session.<a href="#section-4.2.1-3" class="pilcrow">¶</a></p>
<p id="section-4.2.1-4">If any of the above steps fail, the client <span class="bcp14">MUST</span> 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 <span class="bcp14">MAY</span>
send other, 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 <span class="bcp14">MUST NOT</span> transmit the message to the domain.<a href="#section-4.2.1-4" class="pilcrow">¶</a></p>
<p id="section-4.2.1-5">Following such a failure, the SMTP client <span class="bcp14">MUST</span> send a
non-delivery notification to the reverse-path of the failed
message, as described in <span><a href="https://www.rfc-editor.org/rfc/rfc5321#section-3.6" class="relref">Section 3.6</a> of [<a href="#RFC5321" class="xref">RFC5321</a>]</span>. The
following <span><a href="#RFC5248" class="xref">status codes</a> [<a href="#RFC5248" class="xref">RFC5248</a>]</span> <span class="bcp14">SHOULD</span> be used:<a href="#section-4.2.1-5" class="pilcrow">¶</a></p>
<ul>
<li id="section-4.2.1-6.1">REQUIRETLS not supported by server: 5.7.30 REQUIRETLS
support required<a href="#section-4.2.1-6.1" class="pilcrow">¶</a>
</li>
<li id="section-4.2.1-6.2">Unable to establish TLS-protected SMTP session: 5.7.10
Encryption needed<a href="#section-4.2.1-6.2" class="pilcrow">¶</a>
</li>
</ul>
<p id="section-4.2.1-7">Refer to <a href="#errors" class="xref">Section 5</a> for further requirements regarding
non-delivery messages.<a href="#section-4.2.1-7" class="pilcrow">¶</a></p>
<p id="section-4.2.1-8">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.<a href="#section-4.2.1-8" class="pilcrow">¶</a></p>
</section>
</div>
<div id="maytls">
<section id="section-4.2.2">
<h4 id="name-sending-with-tls-optional">
<a href="#section-4.2.2" class="section-number selfRef">4.2.2. </a><a href="#name-sending-with-tls-optional" class="section-name selfRef">Sending with TLS Optional</a>
</h4>
<p id="section-4.2.2-1">Messages tagged "TLS-Required: No" are handled as
follows. When sending such a message, the sending (client)
MTA <span class="bcp14">MUST</span>:<a href="#section-4.2.2-1" class="pilcrow">¶</a></p>
<ul>
<li id="section-4.2.2-2.1">Look up the SMTP server to which the message is to be
sent, as described in <span>[<a href="#RFC5321" class="xref">RFC5321</a>], <a href="https://www.rfc-editor.org/rfc/rfc5321#section-5.1" class="relref">Section 5.1</a></span>.<a href="#section-4.2.2-2.1" class="pilcrow">¶</a>
</li>
<li id="section-4.2.2-2.2">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.<a href="#section-4.2.2-2.2" class="pilcrow">¶</a>
</li>
</ul>
<p id="section-4.2.2-3">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 <span class="bcp14">MUST</span> be
returned to the sender if message relay fails due to an
inability to negotiate STARTTLS when required by the
server.<a href="#section-4.2.2-3" class="pilcrow">¶</a></p>
<p id="section-4.2.2-4">Since messages tagged with "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.<a href="#section-4.2.2-4" class="pilcrow">¶</a></p>
</section>
</div>
</section>
</div>
<div id="submission">
<section id="section-4.3">
<h3 id="name-requiretls-submission">
<a href="#section-4.3" class="section-number selfRef">4.3. </a><a href="#name-requiretls-submission" class="section-name selfRef">REQUIRETLS Submission</a>
</h3>
<p id="section-4.3-1">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 <span class="bcp14">MUST</span> do so by negotiating STARTTLS
and REQUIRETLS and including the REQUIRETLS option on the MAIL
FROM command, as is done for message relay.<a href="#section-4.3-1" class="pilcrow">¶</a></p>
<p id="section-4.3-2">When TLS is not to be required, the sender <span class="bcp14">MUST</span> include the
TLS-Required header field in the message. SMTP servers
implementing this specification <span class="bcp14">MUST</span> interpret this header
field as described in <a href="#receipt" class="xref">Section 4.1</a>.<a href="#section-4.3-2" class="pilcrow">¶</a></p>
<p id="section-4.3-3">In either case, the decision whether to specify REQUIRETLS
<span class="bcp14">MAY</span> 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 and is beyond
the scope of this specification.<a href="#section-4.3-3" class="pilcrow">¶</a></p>
</section>
</div>
<div id="delivery">
<section id="section-4.4">
<h3 id="name-delivery-of-requiretls-mess">
<a href="#section-4.4" class="section-number selfRef">4.4. </a><a href="#name-delivery-of-requiretls-mess" class="section-name selfRef">Delivery of REQUIRETLS messages</a>
</h3>
<p id="section-4.4-1">Messages are usually retrieved by end users using protocols
other than SMTP such as <span><a href="#RFC3501" class="xref">IMAP</a> [<a href="#RFC3501" class="xref">RFC3501</a>]</span>,
<span><a href="#RFC1939" class="xref">POP</a> [<a href="#RFC1939" class="xref">RFC1939</a>]</span>, or Web mail systems. Mail
delivery agents supporting the REQUIRETLS SMTP option <span class="bcp14">SHOULD</span>
observe the guidelines in <span>[<a href="#RFC8314" class="xref">RFC8314</a>]</span>.<a href="#section-4.4-1" class="pilcrow">¶</a></p>
</section>
</div>
</section>
</div>
<div id="errors">
<section id="section-5">
<h2 id="name-non-delivery-message-handli">
<a href="#section-5" class="section-number selfRef">5. </a><a href="#name-non-delivery-message-handli" class="section-name selfRef">Non-delivery Message Handling</a>
</h2>
<p id="section-5-1">Non-delivery ("bounce") messages usually contain important
metadata about the message to which they refer, including the
original message header. They therefore <span class="bcp14">MUST</span> 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 issue, <span class="bcp14">MUST</span>
also specify the REQUIRETLS SMTP option unless redacted as described below.<a href="#section-5-1" class="pilcrow">¶</a></p>
<p id="section-5-2">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.<a href="#section-5-2" class="pilcrow">¶</a></p>
<p id="section-5-3">If a REQUIRETLS message is bounced, the server <span class="bcp14">MUST</span> behave
as if RET=HDRS was present, as described in <span>[<a href="#RFC3461" class="xref">RFC3461</a>]</span>. If both RET=FULL and REQUIRETLS are
present, the RET=FULL <span class="bcp14">MUST</span> be disregarded. The SMTP client for a
REQUIRETLS bounce message uses an empty MAIL FROM
return-path, as required by <span>[<a href="#RFC5321" class="xref">RFC5321</a>]</span>. When
the MAIL FROM return-path is empty, the REQUIRETLS parameter
<span class="bcp14">SHOULD NOT</span> cause a bounce message to be discarded even if the
next-hop relay does not advertise REQUIRETLS.<a href="#section-5-3" class="pilcrow">¶</a></p>
<p id="section-5-4">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 and that some information
could be leaked if a bounce message is not able to be
transmitted with REQUIRETLS.<a href="#section-5-4" class="pilcrow">¶</a></p>
</section>
</div>
<div id="reorigination">
<section id="section-6">
<h2 id="name-reorigination-consideration">
<a href="#section-6" class="section-number selfRef">6. </a><a href="#name-reorigination-consideration" class="section-name selfRef">Reorigination Considerations</a>
</h2>
<p id="section-6-1">In a number of situations, a <span><a href="#RFC5598" class="xref">mediator</a> [<a href="#RFC5598" class="xref">RFC5598</a>]</span>
originates a new message as a result of an incoming message. These
situations include but are not limited to mailing lists (including
administrative traffic such as message approval requests),
<span><a href="#RFC5228" class="xref">Sieve</a> [<a href="#RFC5228" class="xref">RFC5228</a>]</span>, "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.<a href="#section-6-1" class="pilcrow">¶</a></p>
<p id="section-6-2">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.<a href="#section-6-2" class="pilcrow">¶</a></p>
<p id="section-6-3">User-side mediators (such as use of Sieve rules on a user agent)
typically do not have access to the SMTP 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.<a href="#section-6-3" class="pilcrow">¶</a></p>
</section>
</div>
<div id="IANA">
<section id="section-7">
<h2 id="name-iana-considerations">
<a href="#section-7" class="section-number selfRef">7. </a><a href="#name-iana-considerations" class="section-name selfRef">IANA Considerations</a>
</h2>
<p id="section-7-1">Per this document, IANA has added
the following keyword to the "SMTP Service Extensions" subregistry of the
<span><a href="#MailParams" class="xref">"Mail Parameters" registry</a> [<a href="#MailParams" class="xref">MailParams</a>]</span>:<a href="#section-7-1" class="pilcrow">¶</a></p>
<ul class="ulEmpty">
<li class="ulEmpty" id="section-7-2.1">
<dl class="dlParallel dlCompact" id="section-7-2.1.1">
<dt id="section-7-2.1.1.1">EHLO Keyword:</dt>
<dd style="margin-left: 15.0em" id="section-7-2.1.1.2">REQUIRETLS<a href="#section-7-2.1.1.2" class="pilcrow">¶</a>
</dd>
<dt id="section-7-2.1.1.3">Description:</dt>
<dd style="margin-left: 15.0em" id="section-7-2.1.1.4">Require TLS<a href="#section-7-2.1.1.4" class="pilcrow">¶</a>
</dd>
<dt id="section-7-2.1.1.5">Syntax and parameters:</dt>
<dd style="margin-left: 15.0em" id="section-7-2.1.1.6">(no parameters)<a href="#section-7-2.1.1.6" class="pilcrow">¶</a>
</dd>
<dt id="section-7-2.1.1.7">Additional SMTP verbs:</dt>
<dd style="margin-left: 15.0em" id="section-7-2.1.1.8">none<a href="#section-7-2.1.1.8" class="pilcrow">¶</a>
</dd>
<dt id="section-7-2.1.1.9">MAIL and RCPT parameters:</dt>
<dd style="margin-left: 15.0em" id="section-7-2.1.1.10">REQUIRETLS parameter on MAIL<a href="#section-7-2.1.1.10" class="pilcrow">¶</a>
</dd>
<dt id="section-7-2.1.1.11">Behavior:</dt>
<dd style="margin-left: 15.0em" id="section-7-2.1.1.12">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.<a href="#section-7-2.1.1.12" class="pilcrow">¶</a>
</dd>
<dt id="section-7-2.1.1.13">Command length increment:</dt>
<dd style="margin-left: 15.0em" id="section-7-2.1.1.14">11 characters<a href="#section-7-2.1.1.14" class="pilcrow">¶</a>
</dd>
</dl>
</li>
</ul>
<p id="section-7-3">Per this document, IANA has added an
entry to the "Enumerated Status Codes" subregistry of the <span><a href="#SMTPStatusCodes" class="xref">"Simple Mail Transfer Protocol (SMTP) Enhanced Status
Codes Registry"</a> [<a href="#SMTPStatusCodes" class="xref">SMTPStatusCodes</a>]</span>:<a href="#section-7-3" class="pilcrow">¶</a></p>
<ul class="ulEmpty">
<li class="ulEmpty" id="section-7-4.1">
<dl class="dlParallel dlCompact" id="section-7-4.1.1">
<dt id="section-7-4.1.1.1">Code:</dt>
<dd style="margin-left: 15.0em" id="section-7-4.1.1.2">X.7.30<a href="#section-7-4.1.1.2" class="pilcrow">¶</a>
</dd>
<dt id="section-7-4.1.1.3">Sample Text:</dt>
<dd style="margin-left: 15.0em" id="section-7-4.1.1.4">REQUIRETLS support required<a href="#section-7-4.1.1.4" class="pilcrow">¶</a>
</dd>
<dt id="section-7-4.1.1.5">Associated basic status code:</dt>
<dd style="margin-left: 15.0em" id="section-7-4.1.1.6">550<a href="#section-7-4.1.1.6" class="pilcrow">¶</a>
</dd>
<dt id="section-7-4.1.1.7">Description:</dt>
<dd style="margin-left: 15.0em" id="section-7-4.1.1.8">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.<a href="#section-7-4.1.1.8" class="pilcrow">¶</a>
</dd>
<dt id="section-7-4.1.1.9">Reference:</dt>
<dd style="margin-left: 15.0em" id="section-7-4.1.1.10">RFC 8689<a href="#section-7-4.1.1.10" class="pilcrow">¶</a>
</dd>
<dt id="section-7-4.1.1.11">Submitter:</dt>
<dd style="margin-left: 15.0em" id="section-7-4.1.1.12">J. Fenton<a href="#section-7-4.1.1.12" class="pilcrow">¶</a>
</dd>
<dt id="section-7-4.1.1.13">Change Controller:</dt>
<dd style="margin-left: 15.0em" id="section-7-4.1.1.14">IESG<a href="#section-7-4.1.1.14" class="pilcrow">¶</a>
</dd>
</dl>
</li>
</ul>
<p id="section-7-5">Per this document, IANA has added
an entry to the "Permanent Message Header Field
Names" subregistry of the <span><a href="#MessageHeaders" class="xref">"Message Headers" registry</a> [<a href="#MessageHeaders" class="xref">MessageHeaders</a>]</span> as follows:<a href="#section-7-5" class="pilcrow">¶</a></p>
<ul class="ulEmpty">
<li class="ulEmpty" id="section-7-6.1">
<dl class="dlParallel dlCompact" id="section-7-6.1.1">
<dt id="section-7-6.1.1.1">Header field name:</dt>
<dd style="margin-left: 15.0em" id="section-7-6.1.1.2">TLS-Required<a href="#section-7-6.1.1.2" class="pilcrow">¶</a>
</dd>
<dt id="section-7-6.1.1.3">Applicable protocol:</dt>
<dd style="margin-left: 15.0em" id="section-7-6.1.1.4">mail<a href="#section-7-6.1.1.4" class="pilcrow">¶</a>
</dd>
<dt id="section-7-6.1.1.5">Status:</dt>
<dd style="margin-left: 15.0em" id="section-7-6.1.1.6">standard<a href="#section-7-6.1.1.6" class="pilcrow">¶</a>
</dd>
<dt id="section-7-6.1.1.7">Author/change controller:</dt>
<dd style="margin-left: 15.0em" id="section-7-6.1.1.8">IETF<a href="#section-7-6.1.1.8" class="pilcrow">¶</a>
</dd>
<dt id="section-7-6.1.1.9">Specification document:</dt>
<dd style="margin-left: 15.0em" id="section-7-6.1.1.10">RFC 8689<a href="#section-7-6.1.1.10" class="pilcrow">¶</a>
</dd>
</dl>
</li>
</ul>
</section>
</div>
<div id="Security">
<section id="section-8">
<h2 id="name-security-considerations">
<a href="#section-8" class="section-number selfRef">8. </a><a href="#name-security-considerations" class="section-name selfRef">Security Considerations</a>
</h2>
<p id="section-8-1">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 the wire or explicitly indicating that transport
encryption is not required if it cannot be successfully
negotiated.<a href="#section-8-1" class="pilcrow">¶</a></p>
<p id="section-8-2">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.<a href="#section-8-2" class="pilcrow">¶</a></p>
<div id="Passive">
<section id="section-8.1">
<h3 id="name-passive-attacks">
<a href="#section-8.1" class="section-number selfRef">8.1. </a><a href="#name-passive-attacks" class="section-name selfRef">Passive Attacks</a>
</h3>
<p id="section-8.1-1">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.<a href="#section-8.1-1" class="pilcrow">¶</a></p>
</section>
</div>
<div id="Active">
<section id="section-8.2">
<h3 id="name-active-attacks">
<a href="#section-8.2" class="section-number selfRef">8.2. </a><a href="#name-active-attacks" class="section-name selfRef">Active Attacks</a>
</h3>
<p id="section-8.2-1">Active attacks against 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 href="#section-8.2-1" class="pilcrow">¶</a></p>
<p id="section-8.2-2">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.<a href="#section-8.2-2" class="pilcrow">¶</a></p>
<p id="section-8.2-3">Another active attack involves the spoofing of DNS MX
records of the recipient domain. An attacker 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.<a href="#section-8.2-3" class="pilcrow">¶</a></p>
</section>
</div>
<div id="badactor">
<section id="section-8.3">
<h3 id="name-bad-actor-mtas">
<a href="#section-8.3" class="section-number selfRef">8.3. </a><a href="#name-bad-actor-mtas" class="section-name selfRef">Bad-Actor MTAs</a>
</h3>
<p id="section-8.3-1">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.<a href="#section-8.3-1" class="pilcrow">¶</a></p>
<p id="section-8.3-2">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 <span class="bcp14">MUST</span> be sent using end-to-end content encryption
such as <span><a href="#RFC4880" class="xref">OpenPGP</a> [<a href="#RFC4880" class="xref">RFC4880</a>]</span> or <span><a href="#RFC8551" class="xref">S/MIME</a> [<a href="#RFC8551" class="xref">RFC8551</a>]</span>.<a href="#section-8.3-2" class="pilcrow">¶</a></p>
</section>
</div>
<div id="conflicts">
<section id="section-8.4">
<h3 id="name-policy-conflicts">
<a href="#section-8.4" class="section-number selfRef">8.4. </a><a href="#name-policy-conflicts" class="section-name selfRef">Policy Conflicts</a>
</h3>
<p id="section-8.4-1">In some cases, the use of the TLS-Required header field may conflict
with a recipient domain policy expressed through the <span><a href="#RFC7672" class="xref">DANE</a> [<a href="#RFC7672" class="xref">RFC7672</a>]</span> or <span><a href="#RFC8461" class="xref">MTA-STS</a> [<a href="#RFC8461" class="xref">RFC8461</a>]</span> 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 or MTA-STS.<a href="#section-8.4-1" class="pilcrow">¶</a></p>
</section>
</div>
</section>
</div>
<section id="section-9">
<h2 id="name-references">
<a href="#section-9" class="section-number selfRef">9. </a><a href="#name-references" class="section-name selfRef">References</a>
</h2>
<section id="section-9.1">
<h3 id="name-normative-references">
<a href="#section-9.1" class="section-number selfRef">9.1. </a><a href="#name-normative-references" class="section-name selfRef">Normative References</a>
</h3>
<dl class="references">
<dt id="MailParams">[MailParams]</dt>
<dd>
<span class="refAuthor">IANA</span>, <span class="refTitle">"Mail Parameters"</span>, <span><<a href="http://www.iana.org/assignments/mail-parameters">http://www.iana.org/assignments/mail-parameters</a>></span>. </dd>
<dt id="MessageHeaders">[MessageHeaders]</dt>
<dd>
<span class="refAuthor">IANA</span>, <span class="refTitle">"Permanent Message Header Field Names"</span>, <span><<a href="https://www.iana.org/assignments/message-headers">https://www.iana.org/assignments/message-headers</a>></span>. </dd>
<dt id="RFC2119">[RFC2119]</dt>
<dd>
<span class="refAuthor">Bradner, S.</span>, <span class="refTitle">"Key words for use in RFCs to Indicate Requirement Levels"</span>, <span class="seriesInfo">BCP 14</span>, <span class="seriesInfo">RFC 2119</span>, <span class="seriesInfo">DOI 10.17487/RFC2119</span>, <time datetime="1997-03">March 1997</time>, <span><<a href="https://www.rfc-editor.org/info/rfc2119">https://www.rfc-editor.org/info/rfc2119</a>></span>. </dd>
<dt id="RFC3207">[RFC3207]</dt>
<dd>
<span class="refAuthor">Hoffman, P.</span>, <span class="refTitle">"SMTP Service Extension for Secure SMTP over Transport Layer Security"</span>, <span class="seriesInfo">RFC 3207</span>, <span class="seriesInfo">DOI 10.17487/RFC3207</span>, <time datetime="2002-02">February 2002</time>, <span><<a href="https://www.rfc-editor.org/info/rfc3207">https://www.rfc-editor.org/info/rfc3207</a>></span>. </dd>
<dt id="RFC3461">[RFC3461]</dt>
<dd>
<span class="refAuthor">Moore, K.</span>, <span class="refTitle">"Simple Mail Transfer Protocol (SMTP) Service Extension for Delivery Status Notifications (DSNs)"</span>, <span class="seriesInfo">RFC 3461</span>, <span class="seriesInfo">DOI 10.17487/RFC3461</span>, <time datetime="2003-01">January 2003</time>, <span><<a href="https://www.rfc-editor.org/info/rfc3461">https://www.rfc-editor.org/info/rfc3461</a>></span>. </dd>
<dt id="RFC4033">[RFC4033]</dt>
<dd>
<span class="refAuthor">Arends, R.</span><span class="refAuthor">, Austein, R.</span><span class="refAuthor">, Larson, M.</span><span class="refAuthor">, Massey, D.</span><span class="refAuthor">, and S. Rose</span>, <span class="refTitle">"DNS Security Introduction and Requirements"</span>, <span class="seriesInfo">RFC 4033</span>, <span class="seriesInfo">DOI 10.17487/RFC4033</span>, <time datetime="2005-03">March 2005</time>, <span><<a href="https://www.rfc-editor.org/info/rfc4033">https://www.rfc-editor.org/info/rfc4033</a>></span>. </dd>
<dt id="RFC4034">[RFC4034]</dt>
<dd>
<span class="refAuthor">Arends, R.</span><span class="refAuthor">, Austein, R.</span><span class="refAuthor">, Larson, M.</span><span class="refAuthor">, Massey, D.</span><span class="refAuthor">, and S. Rose</span>, <span class="refTitle">"Resource Records for the DNS Security Extensions"</span>, <span class="seriesInfo">RFC 4034</span>, <span class="seriesInfo">DOI 10.17487/RFC4034</span>, <time datetime="2005-03">March 2005</time>, <span><<a href="https://www.rfc-editor.org/info/rfc4034">https://www.rfc-editor.org/info/rfc4034</a>></span>. </dd>
<dt id="RFC4035">[RFC4035]</dt>
<dd>
<span class="refAuthor">Arends, R.</span><span class="refAuthor">, Austein, R.</span><span class="refAuthor">, Larson, M.</span><span class="refAuthor">, Massey, D.</span><span class="refAuthor">, and S. Rose</span>, <span class="refTitle">"Protocol Modifications for the DNS Security Extensions"</span>, <span class="seriesInfo">RFC 4035</span>, <span class="seriesInfo">DOI 10.17487/RFC4035</span>, <time datetime="2005-03">March 2005</time>, <span><<a href="https://www.rfc-editor.org/info/rfc4035">https://www.rfc-editor.org/info/rfc4035</a>></span>. </dd>
<dt id="RFC5234">[RFC5234]</dt>
<dd>
<span class="refAuthor">Crocker, D., Ed.</span><span class="refAuthor"> and P. Overell</span>, <span class="refTitle">"Augmented BNF for Syntax Specifications: ABNF"</span>, <span class="seriesInfo">STD 68</span>, <span class="seriesInfo">RFC 5234</span>, <span class="seriesInfo">DOI 10.17487/RFC5234</span>, <time datetime="2008-01">January 2008</time>, <span><<a href="https://www.rfc-editor.org/info/rfc5234">https://www.rfc-editor.org/info/rfc5234</a>></span>. </dd>
<dt id="RFC5248">[RFC5248]</dt>
<dd>
<span class="refAuthor">Hansen, T.</span><span class="refAuthor"> and J. Klensin</span>, <span class="refTitle">"A Registry for SMTP Enhanced Mail System Status Codes"</span>, <span class="seriesInfo">BCP 138</span>, <span class="seriesInfo">RFC 5248</span>, <span class="seriesInfo">DOI 10.17487/RFC5248</span>, <time datetime="2008-06">June 2008</time>, <span><<a href="https://www.rfc-editor.org/info/rfc5248">https://www.rfc-editor.org/info/rfc5248</a>></span>. </dd>
<dt id="RFC5321">[RFC5321]</dt>
<dd>
<span class="refAuthor">Klensin, J.</span>, <span class="refTitle">"Simple Mail Transfer Protocol"</span>, <span class="seriesInfo">RFC 5321</span>, <span class="seriesInfo">DOI 10.17487/RFC5321</span>, <time datetime="2008-10">October 2008</time>, <span><<a href="https://www.rfc-editor.org/info/rfc5321">https://www.rfc-editor.org/info/rfc5321</a>></span>. </dd>
<dt id="RFC5322">[RFC5322]</dt>
<dd>
<span class="refAuthor">Resnick, P., Ed.</span>, <span class="refTitle">"Internet Message Format"</span>, <span class="seriesInfo">RFC 5322</span>, <span class="seriesInfo">DOI 10.17487/RFC5322</span>, <time datetime="2008-10">October 2008</time>, <span><<a href="https://www.rfc-editor.org/info/rfc5322">https://www.rfc-editor.org/info/rfc5322</a>></span>. </dd>
<dt id="RFC6125">[RFC6125]</dt>
<dd>
<span class="refAuthor">Saint-Andre, P.</span><span class="refAuthor"> and J. Hodges</span>, <span class="refTitle">"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)"</span>, <span class="seriesInfo">RFC 6125</span>, <span class="seriesInfo">DOI 10.17487/RFC6125</span>, <time datetime="2011-03">March 2011</time>, <span><<a href="https://www.rfc-editor.org/info/rfc6125">https://www.rfc-editor.org/info/rfc6125</a>></span>. </dd>
<dt id="RFC7525">[RFC7525]</dt>
<dd>
<span class="refAuthor">Sheffer, Y.</span><span class="refAuthor">, Holz, R.</span><span class="refAuthor">, and P. Saint-Andre</span>, <span class="refTitle">"Recommendations for Secure Use of Transport Layer Security (TLS) and Datagram Transport Layer Security (DTLS)"</span>, <span class="seriesInfo">BCP 195</span>, <span class="seriesInfo">RFC 7525</span>, <span class="seriesInfo">DOI 10.17487/RFC7525</span>, <time datetime="2015-05">May 2015</time>, <span><<a href="https://www.rfc-editor.org/info/rfc7525">https://www.rfc-editor.org/info/rfc7525</a>></span>. </dd>
<dt id="RFC7672">[RFC7672]</dt>
<dd>
<span class="refAuthor">Dukhovni, V.</span><span class="refAuthor"> and W. Hardaker</span>, <span class="refTitle">"SMTP Security via Opportunistic DNS-Based Authentication of Named Entities (DANE) Transport Layer Security (TLS)"</span>, <span class="seriesInfo">RFC 7672</span>, <span class="seriesInfo">DOI 10.17487/RFC7672</span>, <time datetime="2015-10">October 2015</time>, <span><<a href="https://www.rfc-editor.org/info/rfc7672">https://www.rfc-editor.org/info/rfc7672</a>></span>. </dd>
<dt id="RFC8174">[RFC8174]</dt>
<dd>
<span class="refAuthor">Leiba, B.</span>, <span class="refTitle">"Ambiguity of Uppercase vs Lowercase in RFC 2119 Key Words"</span>, <span class="seriesInfo">BCP 14</span>, <span class="seriesInfo">RFC 8174</span>, <span class="seriesInfo">DOI 10.17487/RFC8174</span>, <time datetime="2017-05">May 2017</time>, <span><<a href="https://www.rfc-editor.org/info/rfc8174">https://www.rfc-editor.org/info/rfc8174</a>></span>. </dd>
<dt id="RFC8314">[RFC8314]</dt>
<dd>
<span class="refAuthor">Moore, K.</span><span class="refAuthor"> and C. Newman</span>, <span class="refTitle">"Cleartext Considered Obsolete: Use of Transport Layer Security (TLS) for Email Submission and Access"</span>, <span class="seriesInfo">RFC 8314</span>, <span class="seriesInfo">DOI 10.17487/RFC8314</span>, <time datetime="2018-01">January 2018</time>, <span><<a href="https://www.rfc-editor.org/info/rfc8314">https://www.rfc-editor.org/info/rfc8314</a>></span>. </dd>
<dt id="RFC8461">[RFC8461]</dt>
<dd>
<span class="refAuthor">Margolis, D.</span><span class="refAuthor">, Risher, M.</span><span class="refAuthor">, Ramakrishnan, B.</span><span class="refAuthor">, Brotman, A.</span><span class="refAuthor">, and J. Jones</span>, <span class="refTitle">"SMTP MTA Strict Transport Security (MTA-STS)"</span>, <span class="seriesInfo">RFC 8461</span>, <span class="seriesInfo">DOI 10.17487/RFC8461</span>, <time datetime="2018-09">September 2018</time>, <span><<a href="https://www.rfc-editor.org/info/rfc8461">https://www.rfc-editor.org/info/rfc8461</a>></span>. </dd>
<dt id="SMTPStatusCodes">[SMTPStatusCodes]</dt>
<dd>
<span class="refAuthor">IANA</span>, <span class="refTitle">"Simple Mail Transfer Protocol (SMTP) Enhanced Status Codes Registry"</span>, <span><<a href="https://www.iana.org/assignments/smtp-enhanced-status-codes">https://www.iana.org/assignments/smtp-enhanced-status-codes</a>></span>. </dd>
</dl>
</section>
<section id="section-9.2">
<h3 id="name-informative-references">
<a href="#section-9.2" class="section-number selfRef">9.2. </a><a href="#name-informative-references" class="section-name selfRef">Informative References</a>
</h3>
<dl class="references">
<dt id="RFC1939">[RFC1939]</dt>
<dd>
<span class="refAuthor">Myers, J.</span><span class="refAuthor"> and M. Rose</span>, <span class="refTitle">"Post Office Protocol - Version 3"</span>, <span class="seriesInfo">STD 53</span>, <span class="seriesInfo">RFC 1939</span>, <span class="seriesInfo">DOI 10.17487/RFC1939</span>, <time datetime="1996-05">May 1996</time>, <span><<a href="https://www.rfc-editor.org/info/rfc1939">https://www.rfc-editor.org/info/rfc1939</a>></span>. </dd>
<dt id="RFC2033">[RFC2033]</dt>
<dd>
<span class="refAuthor">Myers, J.</span>, <span class="refTitle">"Local Mail Transfer Protocol"</span>, <span class="seriesInfo">RFC 2033</span>, <span class="seriesInfo">DOI 10.17487/RFC2033</span>, <time datetime="1996-10">October 1996</time>, <span><<a href="https://www.rfc-editor.org/info/rfc2033">https://www.rfc-editor.org/info/rfc2033</a>></span>. </dd>
<dt id="RFC3501">[RFC3501]</dt>
<dd>
<span class="refAuthor">Crispin, M.</span>, <span class="refTitle">"INTERNET MESSAGE ACCESS PROTOCOL - VERSION 4rev1"</span>, <span class="seriesInfo">RFC 3501</span>, <span class="seriesInfo">DOI 10.17487/RFC3501</span>, <time datetime="2003-03">March 2003</time>, <span><<a href="https://www.rfc-editor.org/info/rfc3501">https://www.rfc-editor.org/info/rfc3501</a>></span>. </dd>
<dt id="RFC4880">[RFC4880]</dt>
<dd>
<span class="refAuthor">Callas, J.</span><span class="refAuthor">, Donnerhacke, L.</span><span class="refAuthor">, Finney, H.</span><span class="refAuthor">, Shaw, D.</span><span class="refAuthor">, and R. Thayer</span>, <span class="refTitle">"OpenPGP Message Format"</span>, <span class="seriesInfo">RFC 4880</span>, <span class="seriesInfo">DOI 10.17487/RFC4880</span>, <time datetime="2007-11">November 2007</time>, <span><<a href="https://www.rfc-editor.org/info/rfc4880">https://www.rfc-editor.org/info/rfc4880</a>></span>. </dd>
<dt id="RFC5228">[RFC5228]</dt>
<dd>
<span class="refAuthor">Guenther, P., Ed.</span><span class="refAuthor"> and T. Showalter, Ed.</span>, <span class="refTitle">"Sieve: An Email Filtering Language"</span>, <span class="seriesInfo">RFC 5228</span>, <span class="seriesInfo">DOI 10.17487/RFC5228</span>, <time datetime="2008-01">January 2008</time>, <span><<a href="https://www.rfc-editor.org/info/rfc5228">https://www.rfc-editor.org/info/rfc5228</a>></span>. </dd>
<dt id="RFC5598">[RFC5598]</dt>
<dd>
<span class="refAuthor">Crocker, D.</span>, <span class="refTitle">"Internet Mail Architecture"</span>, <span class="seriesInfo">RFC 5598</span>, <span class="seriesInfo">DOI 10.17487/RFC5598</span>, <time datetime="2009-07">July 2009</time>, <span><<a href="https://www.rfc-editor.org/info/rfc5598">https://www.rfc-editor.org/info/rfc5598</a>></span>. </dd>
<dt id="RFC6409">[RFC6409]</dt>
<dd>
<span class="refAuthor">Gellens, R.</span><span class="refAuthor"> and J. Klensin</span>, <span class="refTitle">"Message Submission for Mail"</span>, <span class="seriesInfo">STD 72</span>, <span class="seriesInfo">RFC 6409</span>, <span class="seriesInfo">DOI 10.17487/RFC6409</span>, <time datetime="2011-11">November 2011</time>, <span><<a href="https://www.rfc-editor.org/info/rfc6409">https://www.rfc-editor.org/info/rfc6409</a>></span>. </dd>
<dt id="RFC8551">[RFC8551]</dt>
<dd>
<span class="refAuthor">Schaad, J.</span><span class="refAuthor">, Ramsdell, B.</span><span class="refAuthor">, and S. Turner</span>, <span class="refTitle">"Secure/Multipurpose Internet Mail Extensions (S/MIME) Version 4.0 Message Specification"</span>, <span class="seriesInfo">RFC 8551</span>, <span class="seriesInfo">DOI 10.17487/RFC8551</span>, <time datetime="2019-04">April 2019</time>, <span><<a href="https://www.rfc-editor.org/info/rfc8551">https://www.rfc-editor.org/info/rfc8551</a>></span>. </dd>
</dl>
</section>
</section>
<section id="section-appendix.a">
<h2 id="name-examples">
<a href="#section-appendix.a" class="section-number selfRef">Appendix A. </a><a href="#name-examples" class="section-name selfRef">Examples</a>
</h2>
<p id="section-appendix.a-1">This section is informative.<a href="#section-appendix.a-1" class="pilcrow">¶</a></p>
<section id="section-a.1">
<h2 id="name-requiretls-smtp-option">
<a href="#section-a.1" class="section-number selfRef">A.1. </a><a href="#name-requiretls-smtp-option" class="section-name selfRef">REQUIRETLS SMTP Option</a>
</h2>
<p id="section-a.1-1">The TLS-Required SMTP option is used to express the intention of
the sender to have the associated message relayed using TLS. In
the following example, lines beginning with "C:" are transmitted
from the SMTP client to the server, and lines beginning with "S:"
are transmitted in the opposite direction.<a href="#section-a.1-1" class="pilcrow">¶</a></p>
<div class="artwork art-text alignLeft" id="section-a.1-2">
<pre>
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-STARTTLS
S: 250 HELP
C: STARTTLS
S: TLS go ahead
</pre><a href="#section-a.1-2" class="pilcrow">¶</a>
</div>
<p id="section-a.1-3">(at this point TLS negotiation takes place. The remainder of this
session occurs within TLS.)<a href="#section-a.1-3" class="pilcrow">¶</a></p>
<div class="artwork art-text alignLeft" id="section-a.1-4">
<pre>
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
</pre><a href="#section-a.1-4" class="pilcrow">¶</a>
</div>
<p id="section-a.1-5">(message follows)<a href="#section-a.1-5" class="pilcrow">¶</a></p>
<div class="artwork art-text alignLeft" id="section-a.1-6">
<pre>
C: .
S: 250 OK
C: QUIT
</pre><a href="#section-a.1-6" class="pilcrow">¶</a>
</div>
</section>
<section id="section-a.2">
<h2 id="name-tls-required-header-field">
<a href="#section-a.2" class="section-number selfRef">A.2. </a><a href="#name-tls-required-header-field" class="section-name selfRef">TLS-Required Header Field</a>
</h2>
<p id="section-a.2-1">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:<a href="#section-a.2-1" class="pilcrow">¶</a></p>
<div class="artwork art-text alignLeft" id="section-a.2-2">
<pre>
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 </pre><a href="#section-a.2-2" class="pilcrow">¶</a>
</div>
</section>
</section>
<div id="acknowledgements">
<section id="section-appendix.b">
<h2 id="name-acknowledgements">
<a href="#name-acknowledgements" class="section-name selfRef">Acknowledgements</a>
</h2>
<p id="section-appendix.b-1">
The author would like to acknowledge many helpful suggestions on the
ietf-smtp and uta mailing lists, in particular those of Viktor Dukhovni,
Tony Finch, Jeremy Harris, Arvel Hathcock, John Klensin, Barry Leiba, John
Levine, Chris Newman, Rolf Sonneveld, and Per Thorsheim.<a href="#section-appendix.b-1" class="pilcrow">¶</a></p>
</section>
</div>
<div id="authors-addresses">
<section id="section-appendix.c">
<h2 id="name-authors-address">
<a href="#name-authors-address" class="section-name selfRef">Author's Address</a>
</h2>
<address class="vcard">
<div dir="auto" class="left"><span class="fn nameRole">Jim Fenton</span></div>
<div dir="auto" class="left"><span class="org">Altmode Networks</span></div>
<div dir="auto" class="left">
<span class="locality">Los Altos</span>, <span class="region">California</span> <span class="postal-code">94024</span>
</div>
<div dir="auto" class="left"><span class="country-name">United States of America</span></div>
<div class="email">
<span>Email:</span>
<a href="mailto:fenton@bluepopcorn.net" class="email">fenton@bluepopcorn.net</a>
</div>
</address>
</section>
</div>
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