diff --git a/airflow-core/src/airflow/models/deadline.py b/airflow-core/src/airflow/models/deadline.py
index f596c66301498..7af0cca3fc79d 100644
--- a/airflow-core/src/airflow/models/deadline.py
+++ b/airflow-core/src/airflow/models/deadline.py
@@ -242,15 +242,12 @@ def get_simple_context():
 
             return {
                 "dag_run": DAGRunResponse.model_validate(dagrun).model_dump(mode="json"),
-                "deadline": {"id": self.id, "deadline_time": self.deadline_time},
+                "deadline": {"id": str(self.id), "deadline_time": self.deadline_time},
             }
 
         if isinstance(self.callback, TriggererCallback):
-            # Update the callback with context before queuing
-            if "kwargs" not in self.callback.data:
-                self.callback.data["kwargs"] = {}
-            self.callback.data["kwargs"] = (self.callback.data.get("kwargs") or {}) | {
-                "context": get_simple_context()
+            self.callback.data = self.callback.data | {
+                "kwargs": (self.callback.data.get("kwargs") or {}) | {"context": get_simple_context()},
             }
 
             self.callback.queue(session=session)
@@ -258,14 +255,12 @@ def get_simple_context():
             session.flush()
 
         elif isinstance(self.callback, ExecutorCallback):
-            if "kwargs" not in self.callback.data:
-                self.callback.data["kwargs"] = {}
-            self.callback.data["kwargs"] = (self.callback.data.get("kwargs") or {}) | {
-                "context": get_simple_context()
+            self.callback.data = self.callback.data | {
+                "kwargs": (self.callback.data.get("kwargs") or {}) | {"context": get_simple_context()},
+                "deadline_id": str(self.id),
+                "dag_run_id": str(self.dagrun.id),
+                "dag_id": self.dagrun.dag_id,
             }
-            self.callback.data["deadline_id"] = str(self.id)
-            self.callback.data["dag_run_id"] = str(self.dagrun.id)
-            self.callback.data["dag_id"] = self.dagrun.dag_id
 
             self.callback.state = CallbackState.PENDING
             session.add(self.callback)
diff --git a/airflow-core/tests/unit/models/test_deadline.py b/airflow-core/tests/unit/models/test_deadline.py
index 4fc1aada1cc02..99f3d9b127b1b 100644
--- a/airflow-core/tests/unit/models/test_deadline.py
+++ b/airflow-core/tests/unit/models/test_deadline.py
@@ -252,10 +252,73 @@ def test_handle_miss(self, dagrun, session):
         context = callback_kwargs.pop("context")
         assert callback_kwargs == TEST_CALLBACK_KWARGS
 
-        assert context["deadline"]["id"] == deadline_orm.id
+        assert context["deadline"]["id"] == str(deadline_orm.id)
         assert context["deadline"]["deadline_time"].timestamp() == deadline_orm.deadline_time.timestamp()
         assert context["dag_run"] == DAGRunResponse.model_validate(dagrun).model_dump(mode="json")
 
+    @pytest.mark.db_test
+    def test_handle_miss_persists_triggerer_callback_context(self, dagrun, session):
+        deadline_orm = Deadline(
+            deadline_time=DEFAULT_DATE,
+            callback=AsyncCallback(TEST_CALLBACK_PATH, TEST_CALLBACK_KWARGS),
+            dagrun_id=dagrun.id,
+            dag_id=dagrun.dag_id,
+            deadline_alert_id=None,
+        )
+        session.add(deadline_orm)
+        session.flush()
+
+        callback_id = deadline_orm.callback.id
+        deadline_id = deadline_orm.id
+        deadline_time = deadline_orm.deadline_time
+        expected_dag_run = DAGRunResponse.model_validate(dagrun).model_dump(mode="json")
+
+        deadline_orm.handle_miss(session)
+        session.commit()
+        session.expunge_all()
+
+        callback = session.scalar(select(Deadline).where(Deadline.id == deadline_id)).callback
+        assert callback.id == callback_id
+
+        callback_kwargs = callback.data["kwargs"]
+        context = callback_kwargs["context"]
+        assert {
+            key: value for key, value in callback_kwargs.items() if key != "context"
+        } == TEST_CALLBACK_KWARGS
+        assert context["deadline"]["id"] == str(deadline_id)
+        assert context["deadline"]["deadline_time"].timestamp() == deadline_time.timestamp()
+        assert context["dag_run"] == expected_dag_run
+
+        callback.trigger = None
+        session.commit()
+
+    @pytest.mark.db_test
+    def test_handle_miss_persists_executor_callback_routing_data(self, dagrun, session):
+        deadline_orm = Deadline(
+            deadline_time=DEFAULT_DATE,
+            callback=SyncCallback(TEST_CALLBACK_PATH, TEST_CALLBACK_KWARGS),
+            dagrun_id=dagrun.id,
+            dag_id=dagrun.dag_id,
+            deadline_alert_id=None,
+        )
+        session.add(deadline_orm)
+        session.flush()
+
+        callback_id = deadline_orm.callback.id
+        deadline_id = deadline_orm.id
+        dagrun_id = dagrun.id
+        dag_id = dagrun.dag_id
+
+        deadline_orm.handle_miss(session)
+        session.commit()
+        session.expunge_all()
+
+        callback = session.scalar(select(Deadline).where(Deadline.id == deadline_id)).callback
+        assert callback.id == callback_id
+        assert callback.data["dag_run_id"] == str(dagrun_id)
+        assert callback.data["dag_id"] == dag_id
+        assert callback.data["deadline_id"] == str(deadline_id)
+
 
 @pytest.mark.db_test
 class TestCalculatedDeadlineDatabaseCalls: