diff --git a/django/db/models/sql/query.py b/django/db/models/sql/query.py
index 0d1fe5fb43..9fde8496e9 100644
--- a/django/db/models/sql/query.py
+++ b/django/db/models/sql/query.py
@@ -2339,6 +2339,9 @@ class Query(BaseExpression):
             self.append_annotation_mask(group_by_annotations)
             self.select = tuple(values_select.values())
             self.values_select = tuple(values_select)
+            if self.selected is not None:
+                for index, value_select in enumerate(values_select):
+                    self.selected[value_select] = index
         group_by = list(self.select)
         for alias, annotation in self.annotation_select.items():
             if not (group_by_cols := annotation.get_group_by_cols()):
diff --git a/docs/releases/5.2.1.txt b/docs/releases/5.2.1.txt
index 16cbd2c9ba..a4e73841bd 100644
--- a/docs/releases/5.2.1.txt
+++ b/docs/releases/5.2.1.txt
@@ -9,4 +9,6 @@ Django 5.2.1 fixes several bugs in 5.2.
 Bugfixes
 ========
 
-* ...
+* Fixed a regression in Django 5.2 that caused a crash when annotating
+  aggregate expressions over query that uses explicit grouping by transforms
+  followed by field references (:ticket:`36292`).
diff --git a/tests/aggregation/tests.py b/tests/aggregation/tests.py
index 8caefc060c..a8ce6ed1d8 100644
--- a/tests/aggregation/tests.py
+++ b/tests/aggregation/tests.py
@@ -2210,6 +2210,33 @@ class AggregateTestCase(TestCase):
             },
         )
 
+    def test_group_by_transform_column(self):
+        self.assertSequenceEqual(
+            Store.objects.values(
+                "original_opening__date",
+                "name",
+            )
+            .annotate(Count("books"))
+            .order_by("name"),
+            [
+                {
+                    "original_opening__date": datetime.date(1994, 4, 23),
+                    "name": "Amazon.com",
+                    "books__count": 6,
+                },
+                {
+                    "original_opening__date": datetime.date(2001, 3, 15),
+                    "name": "Books.com",
+                    "books__count": 4,
+                },
+                {
+                    "original_opening__date": datetime.date(1945, 4, 25),
+                    "name": "Mamma and Pappa's Books",
+                    "books__count": 3,
+                },
+            ],
+        )
+
     def test_group_by_reference_subquery(self):
         author_qs = (
             Author.objects.annotate(publisher_id=F("book__publisher"))