From 72ce82abcf9051b18a05350936de7ecab7306662 Mon Sep 17 00:00:00 2001
From: "Miss Skeleton (bot)" <31488909+miss-islington@users.noreply.github.com>
Date: Mon, 19 Oct 2020 16:11:37 -0700
Subject: [PATCH] bpo-27321 Fix email.generator.py to not replace a
 non-existent header. (GH-18074)

This PR replaces GH-1977. The reason for the replacement is two-fold.

The fix itself is different is that if the CTE header doesn't exist in the original message, it is inserted. This is important because the new CTE could be quoted-printable whereas the original is implicit 8bit.

Also the tests are different. The test_nonascii_as_string_without_cte test in GH-1977 doesn't actually test the issue in that it passes without the fix. The test_nonascii_as_string_without_content_type_and_cte test is improved here, and even though it doesn't fail without the fix, it is included for completeness.

Automerge-Triggered-By: @warsaw
(cherry picked from commit bf838227c35212709dc43b3c3c57f8e1655c1d24)

Co-authored-by: Mark Sapiro <mark@msapiro.net>
---
 Lib/email/generator.py                                            |    6 +
 Lib/test/test_email/test_email.py                                 |   35 ++++++++++
 Misc/NEWS.d/next/Library/2020-01-19-18-40-26.bpo-27321.8e6SpM.rst |    2 
 3 files changed, 42 insertions(+), 1 deletion(-)
 create mode 100644 Misc/NEWS.d/next/Library/2020-01-19-18-40-26.bpo-27321.8e6SpM.rst

--- a/Lib/email/generator.py
+++ b/Lib/email/generator.py
@@ -186,7 +186,11 @@ class Generator:
         # If we munged the cte, copy the message again and re-fix the CTE.
         if munge_cte:
             msg = deepcopy(msg)
-            msg.replace_header('content-transfer-encoding', munge_cte[0])
+            # Preserve the header order if the CTE header already exists.
+            if msg.get('content-transfer-encoding') is None:
+                msg['Content-Transfer-Encoding'] = munge_cte[0]
+            else:
+                msg.replace_header('content-transfer-encoding', munge_cte[0])
             msg.replace_header('content-type', munge_cte[1])
         # Write the headers.  First we see if the message object wants to
         # handle that itself.  If not, we'll do it generically.
--- a/Lib/test/test_email/test_email.py
+++ b/Lib/test/test_email/test_email.py
@@ -314,6 +314,41 @@ class TestMessageAPI(TestEmailBase):
         g.flatten(msg)
         self.assertEqual(fullrepr, s.getvalue())
 
+    def test_nonascii_as_string_without_cte(self):
+        m = textwrap.dedent("""\
+            MIME-Version: 1.0
+            Content-type: text/plain; charset="iso-8859-1"
+
+            Test if non-ascii messages with no Content-Transfer-Encoding set
+            can be as_string'd:
+            Föö bär
+            """)
+        source = m.encode('iso-8859-1')
+        expected = textwrap.dedent("""\
+            MIME-Version: 1.0
+            Content-type: text/plain; charset="iso-8859-1"
+            Content-Transfer-Encoding: quoted-printable
+
+            Test if non-ascii messages with no Content-Transfer-Encoding set
+            can be as_string'd:
+            F=F6=F6 b=E4r
+            """)
+        msg = email.message_from_bytes(source)
+        self.assertEqual(msg.as_string(), expected)
+
+    def test_nonascii_as_string_without_content_type_and_cte(self):
+        m = textwrap.dedent("""\
+            MIME-Version: 1.0
+
+            Test if non-ascii messages with no Content-Type nor
+            Content-Transfer-Encoding set can be as_string'd:
+            Föö bär
+            """)
+        source = m.encode('iso-8859-1')
+        expected = source.decode('ascii', 'replace')
+        msg = email.message_from_bytes(source)
+        self.assertEqual(msg.as_string(), expected)
+
     def test_as_bytes(self):
         msg = self._msgobj('msg_01.txt')
         with openfile('msg_01.txt') as fp:
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2020-01-19-18-40-26.bpo-27321.8e6SpM.rst
@@ -0,0 +1,2 @@
+Fixed KeyError exception when flattening an email to a string attempts to
+replace a non-existent Content-Transfer-Encoding header.