diff --git a/Grammar/python.gram b/Grammar/python.gram
index 3f16768198f..3d8a39b1d59 100644
--- a/Grammar/python.gram
+++ b/Grammar/python.gram
@@ -170,11 +170,11 @@ for_stmt[stmt_ty]:
         CHECK_VERSION(5, "Async for loops are", _Py_AsyncFor(t, ex, b, el, NEW_TYPE_COMMENT(p, tc), EXTRA)) }
 
 with_stmt[stmt_ty]:
-    | 'with' '(' a=','.with_item+ ')' ':' b=block {
+    | 'with' '(' a=','.with_item+ ','? ')' ':' b=block {
         _Py_With(a, b, NULL, EXTRA) }
     | 'with' a=','.with_item+ ':' tc=[TYPE_COMMENT] b=block {
         _Py_With(a, b, NEW_TYPE_COMMENT(p, tc), EXTRA) }
-    | ASYNC 'with' '(' a=','.with_item+ ')' ':' b=block {
+    | ASYNC 'with' '(' a=','.with_item+ ','? ')' ':' b=block {
        CHECK_VERSION(5, "Async with statements are", _Py_AsyncWith(a, b, NULL, EXTRA)) }
     | ASYNC 'with' a=','.with_item+ ':' tc=[TYPE_COMMENT] b=block {
        CHECK_VERSION(5, "Async with statements are", _Py_AsyncWith(a, b, NEW_TYPE_COMMENT(p, tc), EXTRA)) }
diff --git a/Lib/test/test_grammar.py b/Lib/test/test_grammar.py
index 922a5166ec1..c24d3529490 100644
--- a/Lib/test/test_grammar.py
+++ b/Lib/test/test_grammar.py
@@ -1,7 +1,7 @@
 # Python test set -- part 1, grammar.
 # This just tests whether the parser accepts them all.
 
-from test.support import check_syntax_error, check_syntax_warning
+from test.support import check_syntax_error, check_syntax_warning, use_old_parser
 import inspect
 import unittest
 import sys
@@ -1694,6 +1694,70 @@ class GrammarTests(unittest.TestCase):
         with manager() as x, manager():
             pass
 
+        if not use_old_parser():
+            test_cases = [
+                """if 1:
+                    with (
+                        manager()
+                    ):
+                        pass
+                """,
+                """if 1:
+                    with (
+                        manager() as x
+                    ):
+                        pass
+                """,
+                """if 1:
+                    with (
+                        manager() as (x, y),
+                        manager() as z,
+                    ):
+                        pass
+                """,
+                """if 1:
+                    with (
+                        manager(),
+                        manager()
+                    ):
+                        pass
+                """,
+                """if 1:
+                    with (
+                        manager() as x,
+                        manager() as y
+                    ):
+                        pass
+                """,
+                """if 1:
+                    with (
+                        manager() as x,
+                        manager()
+                    ):
+                        pass
+                """,
+                """if 1:
+                    with (
+                        manager() as x,
+                        manager() as y,
+                        manager() as z,
+                    ):
+                        pass
+                """,
+                """if 1:
+                    with (
+                        manager() as x,
+                        manager() as y,
+                        manager(),
+                    ):
+                        pass
+                """,
+            ]
+            for case in test_cases:
+                with self.subTest(case=case):
+                    compile(case, "<string>", "exec")
+
+
     def test_if_else_expr(self):
         # Test ifelse expressions in various cases
         def _checkeval(msg, ret):
diff --git a/Parser/pegen/parse.c b/Parser/pegen/parse.c
index 3b518ee2637..d86390839d5 100644
--- a/Parser/pegen/parse.c
+++ b/Parser/pegen/parse.c
@@ -3031,9 +3031,9 @@ for_stmt_rule(Parser *p)
 }
 
 // with_stmt:
-//     | 'with' '(' ','.with_item+ ')' ':' block
+//     | 'with' '(' ','.with_item+ ','? ')' ':' block
 //     | 'with' ','.with_item+ ':' TYPE_COMMENT? block
-//     | ASYNC 'with' '(' ','.with_item+ ')' ':' block
+//     | ASYNC 'with' '(' ','.with_item+ ','? ')' ':' block
 //     | ASYNC 'with' ','.with_item+ ':' TYPE_COMMENT? block
 static stmt_ty
 with_stmt_rule(Parser *p)
@@ -3051,13 +3051,15 @@ with_stmt_rule(Parser *p)
     UNUSED(start_lineno); // Only used by EXTRA macro
     int start_col_offset = p->tokens[mark]->col_offset;
     UNUSED(start_col_offset); // Only used by EXTRA macro
-    { // 'with' '(' ','.with_item+ ')' ':' block
+    { // 'with' '(' ','.with_item+ ','? ')' ':' block
         asdl_seq * a;
         asdl_seq* b;
         Token * keyword;
         Token * literal;
         Token * literal_1;
         Token * literal_2;
+        void *opt_var;
+        UNUSED(opt_var); // Silence compiler warnings
         if (
             (keyword = _PyPegen_expect_token(p, 519))
             &&
@@ -3065,6 +3067,8 @@ with_stmt_rule(Parser *p)
             &&
             (a = _gather_38_rule(p))
             &&
+            (opt_var = _PyPegen_expect_token(p, 12), 1)
+            &&
             (literal_1 = _PyPegen_expect_token(p, 8))
             &&
             (literal_2 = _PyPegen_expect_token(p, 11))
@@ -3124,7 +3128,7 @@ with_stmt_rule(Parser *p)
         }
         p->mark = mark;
     }
-    { // ASYNC 'with' '(' ','.with_item+ ')' ':' block
+    { // ASYNC 'with' '(' ','.with_item+ ','? ')' ':' block
         asdl_seq * a;
         Token * async_var;
         asdl_seq* b;
@@ -3132,6 +3136,8 @@ with_stmt_rule(Parser *p)
         Token * literal;
         Token * literal_1;
         Token * literal_2;
+        void *opt_var;
+        UNUSED(opt_var); // Silence compiler warnings
         if (
             (async_var = _PyPegen_expect_token(p, ASYNC))
             &&
@@ -3141,6 +3147,8 @@ with_stmt_rule(Parser *p)
             &&
             (a = _gather_42_rule(p))
             &&
+            (opt_var = _PyPegen_expect_token(p, 12), 1)
+            &&
             (literal_1 = _PyPegen_expect_token(p, 8))
             &&
             (literal_2 = _PyPegen_expect_token(p, 11))