bpo-35926: Add support for OpenSSL 1.1.1b on Windows (GH-11779)

2 files changed, 19 insertions, 4 deletions

diff --git a/Lib/test/test_asyncio/test_sslproto.py b/Lib/test/test_asyncio/test_sslproto.py
index 7bc2ccf0bd..079b255855 100644
--- a/Lib/test/test_asyncio/test_sslproto.py
+++ b/Lib/test/test_asyncio/test_sslproto.py
@@ -497,8 +497,8 @@ class BaseStartTLS(func_tests.FunctionalTestCaseMixin):
 
         server_context = test_utils.simple_server_sslcontext()
         client_context = test_utils.simple_client_sslcontext()
-        if sys.platform.startswith('freebsd'):
-            # bpo-35031: Some FreeBSD buildbots fail to run this test
+        if sys.platform.startswith('freebsd') or sys.platform.startswith('win'):
+            # bpo-35031: Some FreeBSD and Windows buildbots fail to run this test
             # as the eof was not being received by the server if the payload
             # size is not big enough. This behaviour only appears if the
             # client is using TLS1.3.
diff --git a/Lib/test/test_ssl.py b/Lib/test/test_ssl.py
index 5b53b8250f..d48d6e5569 100644
--- a/Lib/test/test_ssl.py
+++ b/Lib/test/test_ssl.py
@@ -2188,7 +2188,7 @@ class ThreadedEchoServer(threading.Thread):
                     self.sock, server_side=True)
                 self.server.selected_npn_protocols.append(self.sslconn.selected_npn_protocol())
                 self.server.selected_alpn_protocols.append(self.sslconn.selected_alpn_protocol())
-            except (ConnectionResetError, BrokenPipeError) as e:
+            except (ConnectionResetError, BrokenPipeError, ConnectionAbortedError) as e:
                 # We treat ConnectionResetError as though it were an
                 # SSLError - OpenSSL on Ubuntu abruptly closes the
                 # connection when asked to use an unsupported protocol.
@@ -2196,6 +2196,9 @@ class ThreadedEchoServer(threading.Thread):
                 # BrokenPipeError is raised in TLS 1.3 mode, when OpenSSL
                 # tries to send session tickets after handshake.
                 # https://github.com/openssl/openssl/issues/6342
+                #
+                # ConnectionAbortedError is raised in TLS 1.3 mode, when OpenSSL
+                # tries to send session tickets after handshake when using WinSock.
                 self.server.conn_errors.append(str(e))
                 if self.server.chatty:
                     handle_error("\n server:  bad connection attempt from " + repr(self.addr) + ":\n")
@@ -2326,7 +2329,7 @@ class ThreadedEchoServer(threading.Thread):
                             sys.stdout.write(" server: read %r (%s), sending back %r (%s)...\n"
                                              % (msg, ctype, msg.lower(), ctype))
                         self.write(msg.lower())
-                except ConnectionResetError:
+                except (ConnectionResetError, ConnectionAbortedError):
                     # XXX: OpenSSL 1.1.1 sometimes raises ConnectionResetError
                     # when connection is not shut down gracefully.
                     if self.server.chatty and support.verbose:
@@ -2336,6 +2339,18 @@ class ThreadedEchoServer(threading.Thread):
                         )
                     self.close()
                     self.running = False
+                except ssl.SSLError as err:
+                    # On Windows sometimes test_pha_required_nocert receives the
+                    # PEER_DID_NOT_RETURN_A_CERTIFICATE exception
+                    # before the 'tlsv13 alert certificate required' exception.
+                    # If the server is stopped when PEER_DID_NOT_RETURN_A_CERTIFICATE
+                    # is received test_pha_required_nocert fails with ConnectionResetError
+                    # because the underlying socket is closed
+                    if 'PEER_DID_NOT_RETURN_A_CERTIFICATE' == err.reason:
+                        if self.server.chatty and support.verbose:
+                            sys.stdout.write(err.args[1])
+                        # test_pha_required_nocert is expecting this exception
+                        raise ssl.SSLError('tlsv13 alert certificate required')
                 except OSError:
                     if self.server.chatty:
                         handle_error("Test server failure:\n")