diff --git a/Lib/test/test_grammar.py b/Lib/test/test_grammar.py
index 0be869e..c15f10b 100644
--- a/Lib/test/test_grammar.py
+++ b/Lib/test/test_grammar.py
@@ -279,6 +279,7 @@ class GrammarTests(unittest.TestCase):
 
     from test.support import check_syntax_error
     from test.support.warnings_helper import check_syntax_warning
+    from test.support.warnings_helper import check_no_warnings
 
     # single_input: NEWLINE | simple_stmt | compound_stmt NEWLINE
     # XXX can't test in a script -- this rule is only used when interactive
@@ -1194,7 +1195,7 @@ def test_assert(self):
 
     # these tests fail if python is run with -O, so check __debug__
     @unittest.skipUnless(__debug__, "Won't work if __debug__ is False")
-    def testAssert2(self):
+    def test_assert_failures(self):
         try:
             assert 0, "msg"
         except AssertionError as e:
@@ -1209,11 +1210,36 @@ def testAssert2(self):
         else:
             self.fail("AssertionError not raised by 'assert False'")
 
+    def test_assert_syntax_warnings(self):
+        # Ensure that we warn users if they provide a non-zero length tuple as
+        # the assertion test.
         self.check_syntax_warning('assert(x, "msg")',
                                   'assertion is always true')
+        self.check_syntax_warning('assert(False, "msg")',
+                                  'assertion is always true')
+        self.check_syntax_warning('assert(False,)',
+                                  'assertion is always true')
+
+        with self.check_no_warnings(category=SyntaxWarning):
+            compile('assert x, "msg"', '<testcase>', 'exec')
+            compile('assert False, "msg"', '<testcase>', 'exec')
+
+    def test_assert_warning_promotes_to_syntax_error(self):
+        # If SyntaxWarning is configured to be an error, it actually raises a
+        # SyntaxError.
+        # https://bugs.python.org/issue35029
         with warnings.catch_warnings():
             warnings.simplefilter('error', SyntaxWarning)
-            compile('assert x, "msg"', '<testcase>', 'exec')
+            try:
+                compile('assert x, "msg" ', '<testcase>', 'exec')
+            except SyntaxError:
+                self.fail('SyntaxError incorrectly raised for \'assert x, "msg"\'')
+            with self.assertRaises(SyntaxError):
+                compile('assert(x, "msg")', '<testcase>', 'exec')
+            with self.assertRaises(SyntaxError):
+                compile('assert(False, "msg")', '<testcase>', 'exec')
+            with self.assertRaises(SyntaxError):
+                compile('assert(False,)', '<testcase>', 'exec')
 
 
     ### compound_stmt: if_stmt | while_stmt | for_stmt | try_stmt | funcdef | classdef
diff --git a/Misc/NEWS.d/next/Core and Builtins/2021-03-15-07-50-30.bpo-43497.Uc5ZCJ.rst b/Misc/NEWS.d/next/Core and Builtins/2021-03-15-07-50-30.bpo-43497.Uc5ZCJ.rst
new file mode 100644
index 0000000..d30677f
--- /dev/null
+++ b/Misc/NEWS.d/next/Core and Builtins/2021-03-15-07-50-30.bpo-43497.Uc5ZCJ.rst
@@ -0,0 +1 @@
+Emit SyntaxWarnings for assertions with tuple constants, this is a regression introduced in python3.7
\ No newline at end of file
diff --git a/Python/compile.c b/Python/compile.c
index ea1bf6b..a1260aa 100644
--- a/Python/compile.c
+++ b/Python/compile.c
@@ -3355,10 +3355,12 @@ compiler_assert(struct compiler *c, stmt_ty s)
 {
     basicblock *end;
 
-    if (c->c_optimize)
-        return 1;
-    if (s->v.Assert.test->kind == Tuple_kind &&
-        asdl_seq_LEN(s->v.Assert.test->v.Tuple.elts) > 0)
+    /* Always emit a warning if the test is a non-zero length tuple */
+    if ((s->v.Assert.test->kind == Tuple_kind &&
+        asdl_seq_LEN(s->v.Assert.test->v.Tuple.elts) > 0) ||
+        (s->v.Assert.test->kind == Constant_kind &&
+         PyTuple_Check(s->v.Assert.test->v.Constant.value) &&
+         PyTuple_Size(s->v.Assert.test->v.Constant.value) > 0))
     {
         if (!compiler_warn(c, "assertion is always true, "
                               "perhaps remove parentheses?"))
@@ -3366,6 +3368,8 @@ compiler_assert(struct compiler *c, stmt_ty s)
             return 0;
         }
     }
+    if (c->c_optimize)
+        return 1;
     end = compiler_new_block(c);
     if (end == NULL)
         return 0;