diff --git a/rclpy/rclpy/executors.py b/rclpy/rclpy/executors.py
index 5b94e3d36..d45d7aeba 100644
--- a/rclpy/rclpy/executors.py
+++ b/rclpy/rclpy/executors.py
@@ -520,9 +520,6 @@ def _wait_for_ready_callbacks(
             entity_count = NumberOfEntities(
                 len(subscriptions), len(guards), len(timers), len(clients), len(services))
 
-            for waitable in waitables:
-                entity_count += waitable.get_num_entities()
-
             # Construct a wait set
             with _WaitSet() as wait_set, ExitStack() as context_stack:
                 sub_capsules = []
@@ -560,6 +557,13 @@ def _wait_for_ready_callbacks(
                     except InvalidHandle:
                         entity_count.num_guard_conditions -= 1
 
+                for waitable in waitables:
+                    try:
+                        context_stack.enter_context(waitable)
+                        entity_count += waitable.get_num_entities()
+                    except InvalidHandle:
+                        pass
+
                 context_capsule = context_stack.enter_context(self._context.handle)
                 _rclpy.rclpy_wait_set_init(
                     wait_set,
diff --git a/rclpy/rclpy/qos_event.py b/rclpy/rclpy/qos_event.py
index 504a9ae90..a0e6022b3 100644
--- a/rclpy/rclpy/qos_event.py
+++ b/rclpy/rclpy/qos_event.py
@@ -177,6 +177,14 @@ def add_to_wait_set(self, wait_set):
         with self._event_handle as event_capsule:
             self._event_index = _rclpy.rclpy_wait_set_add_entity('event', wait_set, event_capsule)
 
+    def __enter__(self):
+        """Mark event as in-use to prevent destruction while waiting on it."""
+        self._event_handle.__enter__()
+
+    def __exit__(self, t, v, tb):
+        """Mark event as not-in-use to allow destruction after waiting on it."""
+        self._event_handle.__exit__(t, v, tb)
+
     def destroy(self):
         self._event_handle.destroy()
 
diff --git a/rclpy/rclpy/waitable.py b/rclpy/rclpy/waitable.py
index a42211ed4..fb70bb107 100644
--- a/rclpy/rclpy/waitable.py
+++ b/rclpy/rclpy/waitable.py
@@ -65,6 +65,14 @@ def __init__(self, callback_group):
         # List of Futures that have callbacks needing execution
         self._futures = []
 
+    def __enter__(self):
+        """Implement to mark entities as in-use to prevent destruction while waiting on them."""
+        pass
+
+    def __exit__(self, t, v, tb):
+        """Implement to mark entities as not-in-use to allow destruction after waiting on them."""
+        pass
+
     def add_future(self, future):
         self._futures.append(future)