diff --git a/Lib/http/client.py b/Lib/http/client.py
index 08311d7bb82..939615b2fb4 100644
--- a/Lib/http/client.py
+++ b/Lib/http/client.py
@@ -864,7 +864,7 @@ class HTTPConnection:
                 if encode:
                     datablock = datablock.encode("iso-8859-1")
                 self.sock.sendall(datablock)
-
+            return
         try:
             self.sock.sendall(data)
         except TypeError:
diff --git a/Lib/test/test_httplib.py b/Lib/test/test_httplib.py
index a2f141ec5e8..b3688af8950 100644
--- a/Lib/test/test_httplib.py
+++ b/Lib/test/test_httplib.py
@@ -373,6 +373,27 @@ class BasicTest(TestCase):
         conn.send(io.BytesIO(expected))
         self.assertEqual(expected, sock.data)
 
+    def test_send_updating_file(self):
+        def data():
+            yield 'data'
+            yield None
+            yield 'data_two'
+
+        class UpdatingFile():
+            mode = 'r'
+            d = data()
+            def read(self, blocksize=-1):
+                return self.d.__next__()
+
+        expected = b'data'
+
+        conn = client.HTTPConnection('example.com')
+        sock = FakeSocket("")
+        conn.sock = sock
+        conn.send(UpdatingFile())
+        self.assertEqual(sock.data, expected)
+
+
     def test_send_iter(self):
         expected = b'GET /foo HTTP/1.1\r\nHost: example.com\r\n' \
                    b'Accept-Encoding: identity\r\nContent-Length: 11\r\n' \
diff --git a/Misc/NEWS b/Misc/NEWS
index 90c609e31df..c2f9e7a2b6e 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -34,6 +34,9 @@ Core and Builtins
 Library
 -------
 
+- Issue #16658: add missing return to HTTPConnection.send()
+  Patch by Jeff Knupp.
+
 - Issue #9556: Allowed specifying a time-of-day for a TimedRotatingFileHandler
   to rotate.