diff --git a/exercises/practice/two-bucket/.meta/tests.toml b/exercises/practice/two-bucket/.meta/tests.toml
index d6ff02f53e..a3fe533ece 100644
--- a/exercises/practice/two-bucket/.meta/tests.toml
+++ b/exercises/practice/two-bucket/.meta/tests.toml
@@ -27,6 +27,12 @@ description = "Measure one step using bucket one of size 1 and bucket two of siz
 [eb329c63-5540-4735-b30b-97f7f4df0f84]
 description = "Measure using bucket one of size 2 and bucket two of size 3 - start with bucket one and end with bucket two"
 
+[58d70152-bf2b-46bb-ad54-be58ebe94c03]
+description = "Measure using bucket one much bigger than bucket two"
+
+[9dbe6499-caa5-4a58-b5ce-c988d71b8981]
+description = "Measure using bucket one much smaller than bucket two"
+
 [449be72d-b10a-4f4b-a959-ca741e333b72]
 description = "Not possible to reach the goal"
 
diff --git a/exercises/practice/two-bucket/two_bucket_test.py b/exercises/practice/two-bucket/two_bucket_test.py
index b7d1cc0195..d097866e5b 100644
--- a/exercises/practice/two-bucket/two_bucket_test.py
+++ b/exercises/practice/two-bucket/two_bucket_test.py
@@ -1,6 +1,6 @@
 # These tests are auto-generated with test data from:
 # https://github.com/exercism/problem-specifications/tree/main/exercises/two-bucket/canonical-data.json
-# File last updated on 2023-07-21
+# File last updated on 2025-09-23
 
 import unittest
 
@@ -40,6 +40,12 @@ def test_measure_using_bucket_one_of_size_2_and_bucket_two_of_size_3_start_with_
     ):
         self.assertEqual(measure(2, 3, 3, "one"), (2, "two", 2))
 
+    def test_measure_using_bucket_one_much_bigger_than_bucket_two(self):
+        self.assertEqual(measure(5, 1, 2, "one"), (6, "one", 1))
+
+    def test_measure_using_bucket_one_much_smaller_than_bucket_two(self):
+        self.assertEqual(measure(3, 15, 9, "one"), (6, "two", 0))
+
     def test_not_possible_to_reach_the_goal(self):
         with self.assertRaisesWithMessage(ValueError):
             measure(6, 15, 5, "one")