diff --git a/django/test/testcases.py b/django/test/testcases.py
index b947d70a45..41d01b89b4 100644
--- a/django/test/testcases.py
+++ b/django/test/testcases.py
@@ -1282,11 +1282,18 @@ class TestCase(TransactionTestCase):
         try:
             yield callbacks
         finally:
-            run_on_commit = connections[using].run_on_commit[start_count:]
-            callbacks[:] = [func for sids, func in run_on_commit]
-            if execute:
-                for callback in callbacks:
-                    callback()
+            callback_count = len(connections[using].run_on_commit)
+            while True:
+                run_on_commit = connections[using].run_on_commit[start_count:]
+                callbacks[:] = [func for sids, func in run_on_commit]
+                if execute:
+                    for callback in callbacks:
+                        callback()
+
+                if callback_count == len(connections[using].run_on_commit):
+                    break
+                start_count = callback_count - 1
+                callback_count = len(connections[using].run_on_commit)
 
 
 class CheckCondition:
diff --git a/docs/releases/4.0.txt b/docs/releases/4.0.txt
index 45743c4139..53b738c8ec 100644
--- a/docs/releases/4.0.txt
+++ b/docs/releases/4.0.txt
@@ -368,6 +368,9 @@ Tests
 * The :option:`test --parallel` option now supports the value ``auto`` to run
   one test process for each processor core.
 
+* :meth:`.TestCase.captureOnCommitCallbacks` now captures new callbacks added
+  while executing :func:`.transaction.on_commit` callbacks.
+
 URLs
 ~~~~
 
diff --git a/docs/topics/testing/tools.txt b/docs/topics/testing/tools.txt
index 8e4f077fad..846d428980 100644
--- a/docs/topics/testing/tools.txt
+++ b/docs/topics/testing/tools.txt
@@ -912,6 +912,11 @@ It also provides an additional method:
                 self.assertEqual(mail.outbox[0].subject, 'Contact Form')
                 self.assertEqual(mail.outbox[0].body, 'I like your site')
 
+    .. versionchanged:: 4.0
+
+        In older versions, new callbacks added while executing
+        :func:`.transaction.on_commit` callbacks were not captured.
+
 .. _live-test-server:
 
 ``LiveServerTestCase``
diff --git a/tests/test_utils/tests.py b/tests/test_utils/tests.py
index 44301aaa1b..82ec36ab38 100644
--- a/tests/test_utils/tests.py
+++ b/tests/test_utils/tests.py
@@ -1502,6 +1502,13 @@ class CaptureOnCommitCallbacksTests(TestCase):
 
         self.assertEqual(callbacks, [])
 
+    def test_execute_recursive(self):
+        with self.captureOnCommitCallbacks(execute=True) as callbacks:
+            transaction.on_commit(self.enqueue_callback)
+
+        self.assertEqual(len(callbacks), 2)
+        self.assertIs(self.callback_called, True)
+
 
 class DisallowedDatabaseQueriesTests(SimpleTestCase):
     def test_disallowed_database_connections(self):