diff --git a/tests/test_lifespan.py b/tests/test_lifespan.py
index de584e1a8..2c83199bd 100644
--- a/tests/test_lifespan.py
+++ b/tests/test_lifespan.py
@@ -197,3 +197,33 @@ async def test():
 
     loop = asyncio.new_event_loop()
     loop.run_until_complete(test())
+
+
+@pytest.mark.parametrize("mode", ("auto", "on"))
+@pytest.mark.parametrize("raise_exception", (True, False))
+def test_lifespan_with_failed_shutdown(mode, raise_exception):
+    async def app(scope, receive, send):
+        message = await receive()
+        assert message["type"] == "lifespan.startup"
+        await send({"type": "lifespan.startup.complete"})
+        message = await receive()
+        assert message["type"] == "lifespan.shutdown"
+        await send({"type": "lifespan.shutdown.failed"})
+
+        if raise_exception:
+            # App should be able to re-raise an exception if startup failed.
+            raise RuntimeError()
+
+    async def test():
+        config = Config(app=app, lifespan=mode)
+        lifespan = LifespanOn(config)
+
+        await lifespan.startup()
+        assert not lifespan.startup_failed
+        await lifespan.shutdown()
+        assert lifespan.shutdown_failed
+        assert lifespan.error_occured is raise_exception
+        assert lifespan.should_exit
+
+    loop = asyncio.new_event_loop()
+    loop.run_until_complete(test())
diff --git a/uvicorn/lifespan/on.py b/uvicorn/lifespan/on.py
index 0f0644fef..a8deb7644 100644
--- a/uvicorn/lifespan/on.py
+++ b/uvicorn/lifespan/on.py
@@ -20,6 +20,7 @@ def __init__(self, config: Config) -> None:
         self.receive_queue: "Queue[LifespanReceiveMessage]" = asyncio.Queue()
         self.error_occured = False
         self.startup_failed = False
+        self.shutdown_failed = False
         self.should_exit = False
 
     async def startup(self) -> None:
@@ -43,7 +44,14 @@ async def shutdown(self) -> None:
         self.logger.info("Waiting for application shutdown.")
         await self.receive_queue.put({"type": "lifespan.shutdown"})
         await self.shutdown_event.wait()
-        self.logger.info("Application shutdown complete.")
+
+        if self.shutdown_failed or (
+            self.error_occured and self.config.lifespan == "on"
+        ):
+            self.logger.error("Application shutdown failed. Exiting.")
+            self.should_exit = True
+        else:
+            self.logger.info("Application shutdown complete.")
 
     async def main(self) -> None:
         try:
@@ -56,7 +64,7 @@ async def main(self) -> None:
         except BaseException as exc:
             self.asgi = None
             self.error_occured = True
-            if self.startup_failed:
+            if self.startup_failed or self.shutdown_failed:
                 return
             if self.config.lifespan == "auto":
                 msg = "ASGI 'lifespan' protocol appears unsupported."
@@ -73,6 +81,7 @@ async def send(self, message: LifespanSendMessage) -> None:
             "lifespan.startup.complete",
             "lifespan.startup.failed",
             "lifespan.shutdown.complete",
+            "lifespan.shutdown.failed",
         )
 
         if message["type"] == "lifespan.startup.complete":
@@ -93,5 +102,13 @@ async def send(self, message: LifespanSendMessage) -> None:
             assert not self.shutdown_event.is_set(), STATE_TRANSITION_ERROR
             self.shutdown_event.set()
 
+        elif message["type"] == "lifespan.shutdown.failed":
+            assert self.startup_event.is_set(), STATE_TRANSITION_ERROR
+            assert not self.shutdown_event.is_set(), STATE_TRANSITION_ERROR
+            self.shutdown_event.set()
+            self.shutdown_failed = True
+            if message.get("message"):
+                self.logger.error(message["message"])
+
     async def receive(self) -> LifespanReceiveMessage:
         return await self.receive_queue.get()