#22215: have the smtplib 'quit' command reset the state.

Without this reset, starttls would fail if a connect/starttls was done after a
quit, because smtplib assumed the existing value of emspt_features was
accurate, but it gets reset when starttls completes (and the new value does
not contain the starttls capability, since tls is already started at that
point).  (There may be additional places where this lack of reset was an
issue as well.)

Patch by Milan Oberkirch.

Lib/smtplib.py

@@ -754,6 +754,10 @@ class SMTP:
     def quit(self):
         """Terminate the SMTP session."""
         res = self.docmd("quit")
+        # A new EHLO is required after reconnecting with connect()
+        self.ehlo_resp = self.helo_resp = None
+        self.esmtp_features = {}
+        self.does_esmtp = False
         self.close()
         return res
 

Lib/test/test_smtplib.py

@@ -507,6 +507,21 @@ class SMTPSimTests(unittest.TestCase):
     #TODO: add tests for correct AUTH method fallback now that the
     #test infrastructure can support it.
 
+    def test_quit_resets_greeting(self):
+        smtp = smtplib.SMTP(HOST, self.port,
+                            local_hostname='localhost',
+                            timeout=15)
+        code, message = smtp.ehlo()
+        self.assertEqual(code, 250)
+        self.assertIn('size', smtp.esmtp_features)
+        smtp.quit()
+        self.assertNotIn('size', smtp.esmtp_features)
+        smtp.connect(HOST, self.port)
+        self.assertNotIn('size', smtp.esmtp_features)
+        smtp.ehlo_or_helo_if_needed()
+        self.assertIn('size', smtp.esmtp_features)
+        smtp.quit()
+
 
 def test_main(verbose=None):
     test_support.run_unittest(GeneralTests, DebuggingServerTests,

Misc/NEWS

@@ -19,6 +19,10 @@ Core and Builtins
 Library
 -------
 
+- Issue #22216: smtplib now resets its state more completely after a quit.  The
+  most obvious consequence of the previous behavior was a STARTTLS failure
+  during a connect/starttls/quit/connect/starttls sequence.
+
 - Issue #21305: os.urandom now caches a fd to /dev/urandom. This is a PEP 466
   backport from Python 3.