diff --git a/homeassistant/components/plex/__init__.py b/homeassistant/components/plex/__init__.py
index fff6dea3bb4..95fb6e4f09f 100644
--- a/homeassistant/components/plex/__init__.py
+++ b/homeassistant/components/plex/__init__.py
@@ -5,7 +5,14 @@ import json
 import logging
 
 import plexapi.exceptions
-from plexwebsocket import PlexWebsocket
+from plexwebsocket import (
+    SIGNAL_CONNECTION_STATE,
+    SIGNAL_DATA,
+    STATE_CONNECTED,
+    STATE_DISCONNECTED,
+    STATE_STOPPED,
+    PlexWebsocket,
+)
 import requests.exceptions
 import voluptuous as vol
 
@@ -14,7 +21,7 @@ from homeassistant.components.media_player.const import (
     ATTR_MEDIA_CONTENT_ID,
     ATTR_MEDIA_CONTENT_TYPE,
 )
-from homeassistant.config_entries import SOURCE_REAUTH
+from homeassistant.config_entries import ENTRY_STATE_SETUP_RETRY, SOURCE_REAUTH
 from homeassistant.const import (
     ATTR_ENTITY_ID,
     CONF_SOURCE,
@@ -95,11 +102,12 @@ async def async_setup_entry(hass, entry):
             entry, data={**entry.data, PLEX_SERVER_CONFIG: new_server_data}
         )
     except requests.exceptions.ConnectionError as error:
-        _LOGGER.error(
-            "Plex server (%s) could not be reached: [%s]",
-            server_config[CONF_URL],
-            error,
-        )
+        if entry.state != ENTRY_STATE_SETUP_RETRY:
+            _LOGGER.error(
+                "Plex server (%s) could not be reached: [%s]",
+                server_config[CONF_URL],
+                error,
+            )
         raise ConfigEntryNotReady from error
     except plexapi.exceptions.Unauthorized:
         hass.async_create_task(
@@ -142,13 +150,37 @@ async def async_setup_entry(hass, entry):
     hass.data[PLEX_DOMAIN][DISPATCHERS].setdefault(server_id, [])
     hass.data[PLEX_DOMAIN][DISPATCHERS][server_id].append(unsub)
 
-    def update_plex():
-        async_dispatcher_send(hass, PLEX_UPDATE_PLATFORMS_SIGNAL.format(server_id))
+    def plex_websocket_callback(signal, data, error):
+        """Handle callbacks from plexwebsocket library."""
+        if signal == SIGNAL_CONNECTION_STATE:
+
+            if data == STATE_CONNECTED:
+                _LOGGER.debug("Websocket to %s successful", entry.data[CONF_SERVER])
+            elif data == STATE_DISCONNECTED:
+                _LOGGER.debug(
+                    "Websocket to %s disconnected, retrying", entry.data[CONF_SERVER]
+                )
+            # Stopped websockets without errors are expected during shutdown and ignored
+            elif data == STATE_STOPPED and error:
+                _LOGGER.error(
+                    "Websocket to %s failed, aborting [Error: %s]",
+                    entry.data[CONF_SERVER],
+                    error,
+                )
+                asyncio.run_coroutine_threadsafe(
+                    hass.config_entries.async_reload(entry.entry_id), hass.loop
+                )
+
+        elif signal == SIGNAL_DATA:
+            async_dispatcher_send(hass, PLEX_UPDATE_PLATFORMS_SIGNAL.format(server_id))
 
     session = async_get_clientsession(hass)
     verify_ssl = server_config.get(CONF_VERIFY_SSL)
     websocket = PlexWebsocket(
-        plex_server.plex_server, update_plex, session=session, verify_ssl=verify_ssl
+        plex_server.plex_server,
+        plex_websocket_callback,
+        session=session,
+        verify_ssl=verify_ssl,
     )
     hass.data[PLEX_DOMAIN][WEBSOCKETS][server_id] = websocket
 
diff --git a/homeassistant/components/plex/manifest.json b/homeassistant/components/plex/manifest.json
index 29b0fe8038e..f5bbc6ac53c 100644
--- a/homeassistant/components/plex/manifest.json
+++ b/homeassistant/components/plex/manifest.json
@@ -6,7 +6,7 @@
   "requirements": [
       "plexapi==4.1.1",
       "plexauth==0.0.5",
-      "plexwebsocket==0.0.11"
+      "plexwebsocket==0.0.12"
   ],
   "dependencies": ["http"],
   "after_dependencies": ["sonos"],
diff --git a/requirements_all.txt b/requirements_all.txt
index 6b1087502c2..c47f8f0759b 100644
--- a/requirements_all.txt
+++ b/requirements_all.txt
@@ -1116,7 +1116,7 @@ plexapi==4.1.1
 plexauth==0.0.5
 
 # homeassistant.components.plex
-plexwebsocket==0.0.11
+plexwebsocket==0.0.12
 
 # homeassistant.components.plum_lightpad
 plumlightpad==0.0.11
diff --git a/requirements_test_all.txt b/requirements_test_all.txt
index 751fb61f179..49b3b9ea1f7 100644
--- a/requirements_test_all.txt
+++ b/requirements_test_all.txt
@@ -533,7 +533,7 @@ plexapi==4.1.1
 plexauth==0.0.5
 
 # homeassistant.components.plex
-plexwebsocket==0.0.11
+plexwebsocket==0.0.12
 
 # homeassistant.components.plum_lightpad
 plumlightpad==0.0.11
diff --git a/tests/components/plex/helpers.py b/tests/components/plex/helpers.py
index 8055ab0d5b1..a20d70fbb7e 100644
--- a/tests/components/plex/helpers.py
+++ b/tests/components/plex/helpers.py
@@ -1,7 +1,8 @@
 """Helper methods for Plex tests."""
+from plexwebsocket import SIGNAL_DATA
 
 
 def trigger_plex_update(mock_websocket):
     """Call the websocket callback method."""
     callback = mock_websocket.call_args[0][1]
-    callback()
+    callback(SIGNAL_DATA, None, None)