diff --git a/exercises/practice/swift-scheduling/.meta/tests.toml b/exercises/practice/swift-scheduling/.meta/tests.toml
index ef2aa5166bc..f2475c9ea0b 100644
--- a/exercises/practice/swift-scheduling/.meta/tests.toml
+++ b/exercises/practice/swift-scheduling/.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.
 
 [1d0e6e72-f370-408c-bc64-5dafa9c6da73]
 description = "NOW translates to two hours later"
@@ -49,3 +56,6 @@ description = "Q4 in the second quarter translates to the last workday of the fo
 
 [c920886c-44ad-4d34-a156-dc4176186581]
 description = "Q3 in the fourth quarter translates to the last workday of the third quarter of next year"
+
+[7c8f1616-be62-417e-bbd5-a60fa743eccc]
+description = "Q2 starting in the last month of the second quarter translates to the last workday of the second quarter of this year"
diff --git a/exercises/practice/swift-scheduling/swift_scheduling_test.py b/exercises/practice/swift-scheduling/swift_scheduling_test.py
index 234f7feec0d..3cbe38d911e 100644
--- a/exercises/practice/swift-scheduling/swift_scheduling_test.py
+++ b/exercises/practice/swift-scheduling/swift_scheduling_test.py
@@ -1,6 +1,6 @@
 # These tests are auto-generated with test data from:
 # https://github.com/exercism/problem-specifications/tree/main/exercises/swift-scheduling/canonical-data.json
-# File last updated on 2026-02-19
+# File last updated on 2026-09-30
 
 import unittest
 
@@ -108,3 +108,10 @@ def test_q3_in_the_fourth_quarter_translates_to_the_last_workday_of_the_third_qu
         self.assertEqual(
             delivery_date("2022-10-06T11:00:00", "Q3"), "2023-09-29T08:00:00"
         )
+
+    def test_q2_starting_in_the_last_month_of_the_second_quarter_translates_to_the_last_workday_of_the_second_quarter_of_this_year(
+        self,
+    ):
+        self.assertEqual(
+            delivery_date("2019-06-15T09:50:00", "Q2"), "2019-06-28T08:00:00"
+        )