diff --git a/exercises/practice/connect/.meta/tests.toml b/exercises/practice/connect/.meta/tests.toml
index 6ada87732c..951b87e5c4 100644
--- a/exercises/practice/connect/.meta/tests.toml
+++ b/exercises/practice/connect/.meta/tests.toml
@@ -30,6 +30,12 @@ description = "nobody wins crossing adjacent angles"
 [cd61c143-92f6-4a8d-84d9-cb2b359e226b]
 description = "X wins crossing from left to right"
 
+[495e33ed-30a9-4012-b46e-d7c4d5fe13c3]
+description = "X wins with left-hand dead end fork"
+
+[ab167ab0-4a98-4d0f-a1c0-e1cddddc3d58]
+description = "X wins with right-hand dead end fork"
+
 [73d1eda6-16ab-4460-9904-b5f5dd401d0b]
 description = "O wins crossing from top to bottom"
 
diff --git a/exercises/practice/connect/connect_test.py b/exercises/practice/connect/connect_test.py
index 9214cda980..2ed17be4f4 100644
--- a/exercises/practice/connect/connect_test.py
+++ b/exercises/practice/connect/connect_test.py
@@ -1,6 +1,6 @@
 # These tests are auto-generated with test data from:
 # https://github.com/exercism/problem-specifications/tree/main/exercises/connect/canonical-data.json
-# File last updated on 2026-02-19
+# File last updated on 2026-05-01
 
 import unittest
 
@@ -75,6 +75,26 @@ def test_x_wins_crossing_from_left_to_right(self):
         winner = game.get_winner()
         self.assertEqual(winner, "X")
 
+    def test_x_wins_with_left_hand_dead_end_fork(self):
+        game = ConnectGame(
+            """. . X .
+                X X . .
+                 . X X X
+                  O O O O"""
+        )
+        winner = game.get_winner()
+        self.assertEqual(winner, "X")
+
+    def test_x_wins_with_right_hand_dead_end_fork(self):
+        game = ConnectGame(
+            """. . X X
+                X X . .
+                 . X X .
+                  O O O O"""
+        )
+        winner = game.get_winner()
+        self.assertEqual(winner, "X")
+
     def test_o_wins_crossing_from_top_to_bottom(self):
         game = ConnectGame(
             """. O . .