Index: Lib/test/test_grammar.py
===================================================================
--- Lib/test/test_grammar.py	(revision 80323)
+++ Lib/test/test_grammar.py	(working copy)
@@ -486,7 +486,8 @@
         def f():
             nonlocal x
             nonlocal x, y
-
+    
+    @unittest.skipUnless(__debug__, "Won't work and is irrelevant if __debug__ is False")
     def testAssert(self):
         # assertTruestmt: 'assert' test [',' test]
         assert 1
@@ -496,11 +497,28 @@
         try:
             assert 0, "msg"
         except AssertionError as e:
+            self.assertEqual(len(e.args), 1)
             self.assertEqual(e.args[0], "msg")
         else:
-            if __debug__:
-                self.fail("AssertionError not raised by assert 0")
+            self.fail("AssertionError not raised by assert 0 with message")
+        
+        try:
+            assert False
+        except AssertionError as e:
+            self.assertEqual(len(e.args), 0)
+        else:
+            self.fail("AssertionError not raised by 'assert False'")
+        
+        try:
+            assert True
+        except AssertionError as e:
+            self.fail("'assert True' should not have raised an AssertionError")
 
+        try:
+            assert True, 'this should always pass'
+        except AssertionError as e:
+            self.fail("'assert True, msg' should not have raised an AssertionError")
+    
     ### compound_stmt: if_stmt | while_stmt | for_stmt | try_stmt | funcdef | classdef
     # Tested below