diff --git a/exercises/practice/two-bucket/.meta/tests.toml b/exercises/practice/two-bucket/.meta/tests.toml
index 5c7a1fb7..a3fe533e 100644
--- a/exercises/practice/two-bucket/.meta/tests.toml
+++ b/exercises/practice/two-bucket/.meta/tests.toml
@@ -1,6 +1,13 @@
-# This is an auto-generated file. Regular comments will be removed when this
-# file is regenerated. Regenerating will not touch any manually added keys,
-# so comments can be added in a "comment" key.
+# This is an auto-generated file.
+#
+# Regenerating this file via `configlet sync` will:
+# - Recreate every `description` key/value pair
+# - Recreate every `reimplements` key/value pair, where they exist in problem-specifications
+# - Remove any `include = true` key/value pair (an omitted `include` key implies inclusion)
+# - Preserve any other key/value pair
+#
+# As user-added comments (using the # character) will be removed when this file
+# is regenerated, comments can be added via a `comment` key.
 
 [a6f2b4ba-065f-4dca-b6f0-e3eee51cb661]
 description = "Measure using bucket one of size 3 and bucket two of size 5 - start with bucket one"
@@ -20,6 +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.lisp b/exercises/practice/two-bucket/two-bucket-test.lisp
index 41bd60ed..2cf67d9a 100644
--- a/exercises/practice/two-bucket/two-bucket-test.lisp
+++ b/exercises/practice/two-bucket/two-bucket-test.lisp
@@ -73,6 +73,24 @@
            (output (two-bucket:measure bucket-one bucket-two goal start-bucket)))
      (is (equal-alists result output))))
 
+(test measure-using-bucket-one-much-bigger-than-bucket-two
+    (let* ((bucket-one 5)
+           (bucket-two 1)
+           (goal 2)
+           (start-bucket :one)
+           (result '((:moves . 6) (:goal-bucket . :one) (:other-bucket . 1)))
+           (output (two-bucket:measure bucket-one bucket-two goal start-bucket)))
+     (is (equal-alists result output))))
+
+(test measure-using-bucket-one-much-smaller-than-bucket-two
+    (let* ((bucket-one 3)
+           (bucket-two 15)
+           (goal 9)
+           (start-bucket :one)
+           (result '((:moves . 6) (:goal-bucket . :two) (:other-bucket . 0)))
+           (output (two-bucket:measure bucket-one bucket-two goal start-bucket)))
+     (is (equal-alists result output))))
+
 (test not-possible-to-reach-the-goal
     (let ((bucket-one 6)
           (bucket-two 15)