diff --git a/Lib/email/contentmanager.py b/Lib/email/contentmanager.py
index b904ded94c92ef..2b4b8757f46f62 100644
--- a/Lib/email/contentmanager.py
+++ b/Lib/email/contentmanager.py
@@ -146,13 +146,13 @@ def embedded_body(lines): return linesep.join(lines) + linesep
def normal_body(lines): return b'\n'.join(lines) + b'\n'
if cte==None:
# Use heuristics to decide on the "best" encoding.
- try:
- return '7bit', normal_body(lines).decode('ascii')
- except UnicodeDecodeError:
- pass
- if (policy.cte_type == '8bit' and
- max(len(x) for x in lines) <= policy.max_line_length):
- return '8bit', normal_body(lines).decode('ascii', 'surrogateescape')
+ if max(len(x) for x in lines) <= policy.max_line_length:
+ try:
+ return '7bit', normal_body(lines).decode('ascii')
+ except UnicodeDecodeError:
+ pass
+ if policy.cte_type == '8bit':
+ return '8bit', normal_body(lines).decode('ascii', 'surrogateescape')
sniff = embedded_body(lines[:10])
sniff_qp = quoprimime.body_encode(sniff.decode('latin-1'),
policy.max_line_length)
diff --git a/Lib/test/test_email/test_contentmanager.py b/Lib/test/test_email/test_contentmanager.py
index 169058eac83da3..64dca2d017e629 100644
--- a/Lib/test/test_email/test_contentmanager.py
+++ b/Lib/test/test_email/test_contentmanager.py
@@ -329,6 +329,21 @@ def test_set_text_charset_latin_1(self):
self.assertEqual(m.get_payload(decode=True).decode('utf-8'), content)
self.assertEqual(m.get_content(), content)
+ def test_set_text_plain_long_line_heuristics(self):
+ m = self._make_message()
+ content = ("Simple but long message that is over 78 characters"
+ " long to force transfer encoding.\n")
+ raw_data_manager.set_content(m, content)
+ self.assertEqual(str(m), textwrap.dedent("""\
+ Content-Type: text/plain; charset="utf-8"
+ Content-Transfer-Encoding: quoted-printable
+
+ Simple but long message that is over 78 characters long to =
+ force transfer encoding.
+ """))
+ self.assertEqual(m.get_payload(decode=True).decode('utf-8'), content)
+ self.assertEqual(m.get_content(), content)
+
def test_set_text_short_line_minimal_non_ascii_heuristics(self):
m = self._make_message()
content = "et là il est monté sur moi et il commence à m'éto.\n"
diff --git a/Misc/NEWS.d/next/Library/2020-05-11-19-17-23.bpo-40597.4SGfgm.rst b/Misc/NEWS.d/next/Library/2020-05-11-19-17-23.bpo-40597.4SGfgm.rst
new file mode 100644
index 00000000000000..1b9fe609c25b71
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2020-05-11-19-17-23.bpo-40597.4SGfgm.rst
@@ -0,0 +1 @@
+If text content lines are longer than policy.max_line_length, always use a content-encoding to make sure they are wrapped.
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