diff --git a/django/db/models/sql/query.py b/django/db/models/sql/query.py
index 995e89564d..01ff007eda 100644
--- a/django/db/models/sql/query.py
+++ b/django/db/models/sql/query.py
@@ -934,8 +934,14 @@ class Query:
                 if (reuse is None or a in reuse) and j == join
             ]
         if reuse_aliases:
-            self.ref_alias(reuse_aliases[0])
-            return reuse_aliases[0]
+            if join.table_alias in reuse_aliases:
+                reuse_alias = join.table_alias
+            else:
+                # Reuse the most recent alias of the joined table
+                # (a many-to-many relation may be joined multiple times).
+                reuse_alias = reuse_aliases[-1]
+            self.ref_alias(reuse_alias)
+            return reuse_alias
 
         # No reuse is possible, so we need a new alias.
         alias, _ = self.table_alias(join.table_name, create=True, filtered_relation=join.filtered_relation)
diff --git a/tests/annotations/tests.py b/tests/annotations/tests.py
index 4fc7e6f047..c1073d6f41 100644
--- a/tests/annotations/tests.py
+++ b/tests/annotations/tests.py
@@ -569,3 +569,19 @@ class NonAggregateAnnotationTestCase(TestCase):
             Book.objects.annotate(is_book=True)
         with self.assertRaisesMessage(TypeError, msg % ', '.join([str(BooleanField()), 'True'])):
             Book.objects.annotate(BooleanField(), Value(False), is_book=True)
+
+    def test_chaining_annotation_filter_with_m2m(self):
+        qs = Author.objects.filter(
+            name='Adrian Holovaty',
+            friends__age=35,
+        ).annotate(
+            jacob_name=F('friends__name'),
+        ).filter(
+            friends__age=29,
+        ).annotate(
+            james_name=F('friends__name'),
+        ).values('jacob_name', 'james_name')
+        self.assertCountEqual(
+            qs,
+            [{'jacob_name': 'Jacob Kaplan-Moss', 'james_name': 'James Bennett'}],
+        )