EmailMessage objects break when folding malformed header

Bug report

Bug description:

In certain cases, with EmailMessage objects, encoded headers can fold with double line endings, causing breakage of flattened message objects, making messages display improperly in email clients and rendering attachments inaccessible.

Python3.11.11 does not exhibit this behaviour. But numerous other Python versions eg 3.11.9, 3.12.x, 3.10.x and 3.9.x are affected by the bug.

The specific malformation is where:

a header is long
a header is presented with its value presented as RFC 2047 UTF8 base64
when decoded, the header's payload ends with a newline \n

An example of this:

Subject: =?utf-8?B?Vm9pY2Vib3ggRmlybWE6IFRlc3QtTmFjaHJpY2h0IHVtIDEwOjAzOjM1IDA0LjA0LjI1IC0gQUdGRU8gRVMgNTIyIElUIHVwIC0gc3RhaXBzbmV0Cg==?=

Here is a test script which reproduces the problem on many/most recent Python versions:

#!/usr/bin/env python3
"""
Reproduces a bug with flattening email headers whose encoded payloads end in a newline
"""
import sys
from email import policy
from email.parser import Parser, BytesParser, HeaderParser

sampleRaw = """Date: Fri, 04 Apr 2025 10:03:35 +0200\r
From: sender@foo.com\r
Subject: =?utf-8?B?Vm9pY2Vib3ggRmlybWE6IFRlc3QtTmFjaHJpY2h0IHVtIDEwOjAzOjM1IDA0LjA0LjI1IC0gQUdGRU8gRVMgNTIyIElUIHVwIC0gc3RhaXBzbmV0Cg==?=\r
MIME-Version: 1.0\r
Content-Type: multipart/mixed;\r
 boundary="235711131719"\r
To: recipient@bar.com\r
\r
This is a multi-part message in MIME format.\r
--235711131719\r
Content-Type: text/plain; charset=UTF-8; format=flowed\r
Content-Transfer-Encoding: 7bit\r
\r
This is readable part of the body\r
--235711131719--\r
\r
"""

messageObj = Parser(policy=policy.default).parsestr(sampleRaw)

print(sys.version)
print("--------")
print(messageObj.as_string())
print("--------")

Python 3.11.11 flattens the message correctly. Here is an excerpt in/around the Subject: header:

From: sender@foo.com
Subject: Voicebox Firma: Test-Nachricht um 10:03:35 04.04.25 - AGFEO ES 522 IT
 up - =?utf-8?q?staipsnet=0A?=
MIME-Version: 1.0
Content-Type: multipart/mixed;
 boundary="235711131719"
To: recipient@bar.com

This is a multi-part message in MIME format.

As can be seen here, the header has been re-wrapped to quoted-printable (which is fine), the embedded newline is present in the encoded payload, but when the header is folded out, it has only the one line ending. Great.

But other pythons I've tested with come up with:

From: sender@foo.com
Subject: Voicebox Firma: Test-Nachricht um 10:03:35 04.04.25 - AGFEO ES 522 IT
 up - staipsnet

MIME-Version: 1.0
Content-Type: multipart/mixed;
 boundary="235711131719"
To: recipient@bar.com

This is a multi-part message in MIME format.
--235711131719
Content-Type: text/plain; charset=UTF-8; format=flowed
Content-Transfer-Encoding: 7bit

This is readable part of the body

Note the blank line after Subject:.

When messages folded and delivered with this breakage are delivered, MTAs will often add Content-Type: text/plain because the headers after Subject have been lost into the body.

The recipient of the above message will see this formatted as plain text in their viewing pane:

MIME-Version: 1.0
Content-Type: multipart/mixed;
 boundary="235711131719"
To: recipient@bar.com

This is a multi-part message in MIME format.
--235711131719
Content-Type: text/plain; charset=UTF-8; format=flowed
Content-Transfer-Encoding: 7bit

This is readable part of the body

If there were any attachments, their encoded representations will appear after that as gibberish strings, and the mail client won't indicate an attachment is present.

This has potentially serious security implications. If an email delivery chain has python stdlib-based mail processing at or near the end, a carefully structured malicious header can

evade sanitisation
nullify and/or replace headers added upstream in the chain
inject malicious extra headers and MIME-encoded context which may cause subsequent handling steps, and/or the final MUA, to be hijacked for exploit attempts.

Workaround for me has been to subclass a policy, and implement a _fold() method to get the parent class' folding, then .rstrip() it, then add "\r\n" to the end.

CPython versions tested on:

3.12

Operating systems tested on:

Linux

Two further notes:

Newlines within the encoded header also fold with added newlines, allowing any number of extra headers to be injected, and
I am unable to reproduce any of this vulnerable behaviour in a vanilla Python 3.13.2 which I just built from source on Debian.

So now it's both 3.11.11 and 3.13.2 which wrap illegal line breaks (plus a few chars before/after) in quoted-printable encoding. On the other hand, all other Python versions I've tried have the vulnerability.

I’m interested in working on this issue and would appreciate any advice or recommendations you might have to get started.

@rijo7

@rijo7 a good starting point is comparing the behaviour of different Python sub-versions. Some have the vulnerability, some don't.

@davidmcnabnz

@davidmcnabnz could you identify the specific 3.12.x, 3.10.x and 3.9.x versions where you have seen the bug?

It's very possible this was fixed by either #122754 (last month, so just now showing up in the latest Python releases) or #122233 (last summer).

@davidmcnabnz

@davidmcnabnz @medmunds — on the open question of which fix applies: I can't reproduce this on current main (3.16.0a0), and a bisect pins it down.

The reporter's exact script now re-encodes the trailing newline inside the encoded-word (…=0A?=) instead of emitting a spurious blank line; MIME-Version and the rest of the header block stay intact. I checked the same round-trip under the default, SMTP, SMTPUTF8, HTTP and compat32 policies (both as_string() and as_bytes()) — no truncation in any.

Bisecting pins the fix to gh-121650 / PR #122233 (the newline-encoding hardening tracked as CVE-2024-6923): its parent commit still reproduces, the merge itself does not. So of the two candidates floated above, it's #122233 rather than #122754. It forces encoded-word output whenever a header value contains \r/\n, with verify_generated_headers as a backstop (on by default for all policies).

It first shipped in 3.11.10 (#122608) and 3.13.0, so seeing it resolved on 3.11.11 / 3.13.2 lines up, and 3.11.9 predates the fix. Covered by test_keep_encoded_newlines, test_keep_long_encoded_newlines, and test_verify_generated_headers in Lib/test/test_email/test_generator.py.

Looks already-fixed to me — likely closeable, unless anyone still sees it on a maintained branch.

@tonghuaroot

@tonghuaroot Thanks for bisecting. Yes, this report is a duplicate of gh-121650 and is already fixed. It can be closed.

(This example uses base64 rather than quoted-printable encoding in the rfc2047 encoding, but is otherwise exactly the same issue with refolding \n in an encoded-word.)

Navigation Menu

Repository navigation

EmailMessage objects break when folding malformed header #132105

Bug report

Bug description:

CPython versions tested on:

Operating systems tested on:

Metadata

Assignees

Labels

Projects

Milestone

Relationships

Development

EmailMessage objects break when folding malformed header #132105

Description

Bug report

Bug description:

CPython versions tested on:

Operating systems tested on:

Activity

davidmcnabnz commented on Apr 6, 2025

rijo7 commented on Apr 6, 2025

davidmcnabnz commented on Apr 10, 2025

medmunds commented on May 6, 2025

tonghuaroot commented on Jun 23, 2026

medmunds commented on Jun 23, 2026

Metadata

Metadata

Assignees

Labels

Projects

Milestone

Relationships

Development

Issue actions