From 90fa9f4cc090d07bc59717120cc1a5a3a84e1acb Mon Sep 17 00:00:00 2001
From: nessita <124304+nessita@users.noreply.github.com>
Date: Thu, 24 Apr 2025 10:11:16 -0300
Subject: [PATCH] [5.2.x] Fixed #36309 -- Made email alternatives and
 attachments pickleable.

Regression in aba0e541caaa086f183197eaaca0ac20a730bbe4 and in
d5bebc1c26d4c0ec9eaa057aefc5b38649c0ba3b.

Thanks Florent Messa for the report, and Jake Howard and Claude
Paroz for the review.

Backport of 0596263c3136bc26cffa670e5322bd0aa56c4d34 from main.
---
 django/core/mail/message.py |  4 ++--
 docs/releases/5.2.1.txt     |  3 +++
 tests/mail/tests.py         | 18 ++++++++++++++++++
 3 files changed, 23 insertions(+), 2 deletions(-)

diff --git a/django/core/mail/message.py b/django/core/mail/message.py
index adcd9fc504..421e353bfa 100644
--- a/django/core/mail/message.py
+++ b/django/core/mail/message.py
@@ -191,8 +191,8 @@ class SafeMIMEMultipart(MIMEMixin, MIMEMultipart):
         MIMEMultipart.__setitem__(self, name, val)
 
 
-EmailAlternative = namedtuple("Alternative", ["content", "mimetype"])
-EmailAttachment = namedtuple("Attachment", ["filename", "content", "mimetype"])
+EmailAlternative = namedtuple("EmailAlternative", ["content", "mimetype"])
+EmailAttachment = namedtuple("EmailAttachment", ["filename", "content", "mimetype"])
 
 
 class EmailMessage:
diff --git a/docs/releases/5.2.1.txt b/docs/releases/5.2.1.txt
index 82df478d96..a79d61c60a 100644
--- a/docs/releases/5.2.1.txt
+++ b/docs/releases/5.2.1.txt
@@ -48,3 +48,6 @@ Bugfixes
 * Fixed a regression in Django 5.2, introduced when fixing :cve:`2025-26699`,
   where the :tfilter:`wordwrap` template filter did not preserve empty lines
   between paragraphs after wrapping text (:ticket:`36341`).
+
+* Fixed a regression in Django 5.2 that caused a crash when serializing email
+  alternatives or attachments due to named tuple mismatches (:ticket:`36309`).
diff --git a/tests/mail/tests.py b/tests/mail/tests.py
index fe76974862..833b688741 100644
--- a/tests/mail/tests.py
+++ b/tests/mail/tests.py
@@ -1,5 +1,6 @@
 import mimetypes
 import os
+import pickle
 import shutil
 import socket
 import sys
@@ -652,6 +653,23 @@ class MailTests(MailTestsMixin, SimpleTestCase):
 
         self.assertIn(html_content, msg.message().as_string())
 
+    def test_alternatives_and_attachment_serializable(self):
+        html_content = "<p>This is <strong>html</strong></p>"
+        mime_type = "text/html"
+
+        msg = EmailMultiAlternatives(alternatives=[(html_content, mime_type)])
+        msg.attach("test.txt", "This is plain text.", "plain/text")
+
+        # Alternatives and attachments can be serialized.
+        restored = pickle.loads(pickle.dumps(msg))
+
+        self.assertEqual(restored.subject, msg.subject)
+        self.assertEqual(restored.body, msg.body)
+        self.assertEqual(restored.from_email, msg.from_email)
+        self.assertEqual(restored.to, msg.to)
+        self.assertEqual(restored.alternatives, msg.alternatives)
+        self.assertEqual(restored.attachments, msg.attachments)
+
     def test_none_body(self):
         msg = EmailMessage("subject", None, "from@example.com", ["to@example.com"])
         self.assertEqual(msg.body, "")