diff --git a/exercises/practice/bob/.meta/tests.toml b/exercises/practice/bob/.meta/tests.toml
index 6304855792..5299e2895f 100644
--- a/exercises/practice/bob/.meta/tests.toml
+++ b/exercises/practice/bob/.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.
 
 [e162fead-606f-437a-a166-d051915cea8e]
 description = "stating something"
@@ -64,6 +71,7 @@ description = "alternate silence"
 
 [66953780-165b-4e7e-8ce3-4bcb80b6385a]
 description = "multiple line question"
+include = false
 
 [5371ef75-d9ea-4103-bcfa-2da973ddec1b]
 description = "starting with whitespace"
@@ -76,3 +84,7 @@ description = "other whitespace"
 
 [12983553-8601-46a8-92fa-fcaa3bc4a2a0]
 description = "non-question ending with whitespace"
+
+[2c7278ac-f955-4eb4-bf8f-e33eb4116a15]
+description = "multiple line question"
+reimplements = "66953780-165b-4e7e-8ce3-4bcb80b6385a"
diff --git a/exercises/practice/bob/bob_test.py b/exercises/practice/bob/bob_test.py
index faba5f9612..755d5c935e 100644
--- a/exercises/practice/bob/bob_test.py
+++ b/exercises/practice/bob/bob_test.py
@@ -1,6 +1,6 @@
 # These tests are auto-generated with test data from:
 # https://github.com/exercism/problem-specifications/tree/main/exercises/bob/canonical-data.json
-# File last updated on 2023-07-20
+# File last updated on 2025-01-10
 
 import unittest
 
@@ -79,12 +79,6 @@ def test_prolonged_silence(self):
     def test_alternate_silence(self):
         self.assertEqual(response("\t\t\t\t\t\t\t\t\t\t"), "Fine. Be that way!")
 
-    def test_multiple_line_question(self):
-        self.assertEqual(
-            response("\nDoes this cryogenic chamber make me look fat?\nNo."),
-            "Whatever.",
-        )
-
     def test_starting_with_whitespace(self):
         self.assertEqual(response("         hmmmmmmm..."), "Whatever.")
 
@@ -100,3 +94,8 @@ def test_non_question_ending_with_whitespace(self):
         self.assertEqual(
             response("This is a statement ending with whitespace      "), "Whatever."
         )
+
+    def test_multiple_line_question(self):
+        self.assertEqual(
+            response("\nDoes this cryogenic chamber make\n me look fat?"), "Sure."
+        )