diff --git a/irctest/cases.py b/irctest/cases.py
index 74c32818..b5f810f1 100644
--- a/irctest/cases.py
+++ b/irctest/cases.py
@@ -267,6 +267,8 @@ def addClient(self, name=None, show_io=None):
         self.clients[name] = client_mock.ClientMock(name=name,
                 show_io=show_io)
         self.clients[name].connect(self.hostname, self.port)
+        if self.ssl:
+            self.clients[name].starttls()
         return name
 
 
diff --git a/irctest/client_mock.py b/irctest/client_mock.py
index f99cc3c4..6de51579 100644
--- a/irctest/client_mock.py
+++ b/irctest/client_mock.py
@@ -97,7 +97,7 @@ def sendLine(self, line):
         except BrokenPipeError:
             raise ConnectionClosed()
         if self.ssl: # https://bugs.python.org/issue25951
-            assert ret == len(encoded_line), (ret, repr(encoded_line))
+            assert ret is None or ret == len(encoded_line), (ret, repr(encoded_line))
         else:
             assert ret is None, ret
         if self.show_io:
diff --git a/irctest/server_tests/test_regressions.py b/irctest/server_tests/test_regressions.py
index df1fbb5f..20aa0fd4 100644
--- a/irctest/server_tests/test_regressions.py
+++ b/irctest/server_tests/test_regressions.py
@@ -52,7 +52,7 @@ def testCaseChanges(self):
     @cases.SpecificationSelector.requiredBySpecification('IRCv3.2')
     def testTagCap(self):
         # regression test for oragono #754
-        self.connectClient('alice', capabilities=['message-tags', 'batch', 'echo-message', 'server-time'])
+        self.connectClient('alice', capabilities=['message-tags', 'batch', 'echo-message', 'server-time'], skip_if_cap_nak=True)
         self.connectClient('bob')
         self.getMessages(1)
         self.getMessages(2)
diff --git a/irctest/server_tests/test_user_commands.py b/irctest/server_tests/test_user_commands.py
index 55d6539c..235e3f5b 100644
--- a/irctest/server_tests/test_user_commands.py
+++ b/irctest/server_tests/test_user_commands.py
@@ -27,7 +27,7 @@ def testWhoisUser(self):
         self.assertEqual(whois_user.command, RPL_WHOISUSER)
         #  "<client> <nick> <username> <host> * :<realname>"
         self.assertEqual(whois_user.params[1], nick)
-        self.assertEqual(whois_user.params[2], '~' + username)
+        self.assertIn(whois_user.params[2], ['~' + username, username])
         # dumb regression test for oragono/oragono#355:
         self.assertNotIn(whois_user.params[3], [nick, username, '~' + username, realname])
         self.assertEqual(whois_user.params[5], realname)