diff --git a/Lib/email/generator.py b/Lib/email/generator.py
index ae670c2353c858..37310de13d7424 100644
--- a/Lib/email/generator.py
+++ b/Lib/email/generator.py
@@ -403,7 +403,11 @@ class BytesGenerator(Generator):
     """
 
     def write(self, s):
-        self._fp.write(s.encode('ascii', 'surrogateescape'))
+        try:
+            s = s.encode('ascii', 'surrogateescape')
+        except UnicodeEncodeError:
+            s = s.encode('ascii', 'replace')
+        self._fp.write(s)
 
     def _new_buffer(self):
         return BytesIO()
diff --git a/Lib/test/test_email/test_generator.py b/Lib/test/test_email/test_generator.py
index 89e7edeb63a892..d3ddda371d6d97 100644
--- a/Lib/test/test_email/test_generator.py
+++ b/Lib/test/test_email/test_generator.py
@@ -271,6 +271,21 @@ def test_cte_type_7bit_transforms_8bit_cte(self):
         g.flatten(msg)
         self.assertEqual(s.getvalue(), expected)
 
+    def test_flatten_charset_utf8_with_nonascii(self):
+        source = textwrap.dedent("""\
+            Subject: Defective email
+            Content-Type: text/plain; charset=utf-8
+            Content-Transfer-Encoding: 8bit
+
+            I think thatâ**s the way to go.
+            """)
+        expected = source.encode('ascii', 'replace')
+        msg = message_from_string(source)
+        s = io.BytesIO()
+        g = BytesGenerator(s)
+        g.flatten(msg)
+        self.assertEqual(s.getvalue(), expected)
+
     def test_smtputf8_policy(self):
         msg = EmailMessage()
         msg['From'] = "Páolo <főo@bar.com>"
diff --git a/Misc/NEWS.d/next/Library/2020-01-18-23-07-16.bpo-39384.jI9ged.rst b/Misc/NEWS.d/next/Library/2020-01-18-23-07-16.bpo-39384.jI9ged.rst
new file mode 100644
index 00000000000000..d7c609ba597bb5
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2020-01-18-23-07-16.bpo-39384.jI9ged.rst
@@ -0,0 +1,2 @@
+Fixed an issue in email.generator.BytesGenerator.flatten() which would throw
+UnicodeEncodeError with a message with a non-ascii body .