diff --git a/telegram/ext/_application.py b/telegram/ext/_application.py
index 79467b2b4..b18877bc0 100644
--- a/telegram/ext/_application.py
+++ b/telegram/ext/_application.py
@@ -1086,8 +1086,9 @@ class Application(Generic[BT, CCT, UD, CD, BD, JQ], AsyncContextManager["Applica
                     loop.run_until_complete(self.updater.stop())  # type: ignore[union-attr]
                 if self.running:
                     loop.run_until_complete(self.stop())
-                if self.post_stop:
-                    loop.run_until_complete(self.post_stop(self))
+                    # post_stop should be called only if stop was called!
+                    if self.post_stop:
+                        loop.run_until_complete(self.post_stop(self))
                 loop.run_until_complete(self.shutdown())
                 if self.post_shutdown:
                     loop.run_until_complete(self.post_shutdown(self))
diff --git a/telegram/ext/_applicationbuilder.py b/telegram/ext/_applicationbuilder.py
index 783a49858..9fa1fe654 100644
--- a/telegram/ext/_applicationbuilder.py
+++ b/telegram/ext/_applicationbuilder.py
@@ -1334,7 +1334,13 @@ class ApplicationBuilder(Generic[BT, CCT, UD, CD, BD, JQ]):
 
         Tip:
             This can be used for custom stop logic that requires to await coroutines, e.g.
-            sending message to a chat before shutting down the bot
+            sending message to a chat before shutting down the bot.
+
+        Hint:
+            The callback will be called only, if :meth:`Application.stop` was indeed called
+            successfully. For example, if the application is stopped early by calling
+            :meth:`Application.stop_running` within :meth:`post_init`, then the set callback will
+            *not* be called.
 
         Example:
             .. code::
diff --git a/tests/ext/test_application.py b/tests/ext/test_application.py
index 6d1827ae4..714abf853 100644
--- a/tests/ext/test_application.py
+++ b/tests/ext/test_application.py
@@ -2134,7 +2134,6 @@ class TestApplication:
             "app_initialize",
             "updater_initialize",
             "app_shutdown",
-            "post_stop",
             "post_shutdown",
             "updater_shutdown",
         }
@@ -2441,7 +2440,8 @@ class TestApplication:
             app.run_polling(close_loop=False)
 
         # The important part here is that start(_polling) are *not* called!
-        assert called_callbacks == ["post_stop", "post_shutdown"]
+        # post_stop must not be called either, since we never called stop()
+        assert called_callbacks == ["post_shutdown"]
 
         assert len(caplog.records) == 1
         assert caplog.records[-1].name == "telegram.ext.Application"