diff --git a/tests/data/cases/context_managers_39.py b/tests/data/cases/context_managers_39.py
index f4934cb07e4..7f1ee2d576b 100644
--- a/tests/data/cases/context_managers_39.py
+++ b/tests/data/cases/context_managers_39.py
@@ -90,25 +90,6 @@ async def func():
     pass
 
 
-# don't remove the brackets here, it changes the meaning of the code.
-# even though the code will always trigger a runtime error
-with (name_5, name_4), name_5:
-    pass
-
-
-def test_tuple_as_contextmanager():
-    from contextlib import nullcontext
-
-    try:
-        with (nullcontext(),nullcontext()),nullcontext():
-            pass
-    except TypeError: 
-        # test passed
-        pass
-    else:
-        # this should be a type error
-        assert False
-
 # output
 
 
@@ -202,23 +183,3 @@ async def func():
 # don't remove the brackets here, it changes the meaning of the code.
 with (x, y) as z:
     pass
-
-
-# don't remove the brackets here, it changes the meaning of the code.
-# even though the code will always trigger a runtime error
-with (name_5, name_4), name_5:
-    pass
-
-
-def test_tuple_as_contextmanager():
-    from contextlib import nullcontext
-
-    try:
-        with (nullcontext(), nullcontext()), nullcontext():
-            pass
-    except TypeError:
-        # test passed
-        pass
-    else:
-        # this should be a type error
-        assert False
diff --git a/tests/data/cases/tuple_with_stmt.py b/tests/data/cases/tuple_with_stmt.py
new file mode 100644
index 00000000000..885a300f446
--- /dev/null
+++ b/tests/data/cases/tuple_with_stmt.py
@@ -0,0 +1,30 @@
+# don't remove the brackets here, it changes the meaning of the code.
+# even though the code will always trigger a runtime error
+with (name_5, name_4), name_5:
+    pass
+
+
+with c, (a, b):
+    pass
+
+
+with c, (a, b), d:
+    pass
+
+
+with c, (a, b, e, f, g), d:
+    pass
+
+
+def test_tuple_as_contextmanager():
+    from contextlib import nullcontext
+
+    try:
+        with (nullcontext(), nullcontext()), nullcontext():
+            pass
+    except TypeError:
+        # test passed
+        pass
+    else:
+        # this should be a type error
+        assert False