diff --git a/homeassistant/components/plex/__init__.py b/homeassistant/components/plex/__init__.py
index 559f4440aef..59ae14b8ca9 100644
--- a/homeassistant/components/plex/__init__.py
+++ b/homeassistant/components/plex/__init__.py
@@ -35,6 +35,7 @@ from .const import (
     CONF_SERVER_IDENTIFIER,
     DISPATCHERS,
     DOMAIN,
+    INVALID_TOKEN_MESSAGE,
     PLATFORMS,
     PLATFORMS_COMPLETED,
     PLEX_SERVER_CONFIG,
@@ -153,6 +154,11 @@ async def async_setup_entry(hass: HomeAssistant, entry: ConfigEntry) -> bool:
         plexapi.exceptions.BadRequest,
         plexapi.exceptions.NotFound,
     ) as error:
+        if INVALID_TOKEN_MESSAGE in str(error):
+            raise ConfigEntryAuthFailed(
+                "Token not accepted, please reauthenticate Plex server"
+                f" '{entry.data[CONF_SERVER]}'"
+            ) from error
         _LOGGER.error(
             "Login to %s failed, verify token and SSL settings: [%s]",
             entry.data[CONF_SERVER],
diff --git a/homeassistant/components/plex/const.py b/homeassistant/components/plex/const.py
index 3f761c9748a..7936cb6e6c3 100644
--- a/homeassistant/components/plex/const.py
+++ b/homeassistant/components/plex/const.py
@@ -57,3 +57,5 @@ SERVICE_REFRESH_LIBRARY = "refresh_library"
 SERVICE_SCAN_CLIENTS = "scan_for_clients"
 
 PLEX_URI_SCHEME = "plex://"
+
+INVALID_TOKEN_MESSAGE = "Invalid token"
diff --git a/tests/components/plex/test_init.py b/tests/components/plex/test_init.py
index 08b8635829f..bc43a1e0d89 100644
--- a/tests/components/plex/test_init.py
+++ b/tests/components/plex/test_init.py
@@ -360,3 +360,19 @@ async def test_trigger_reauth(
     flows = hass.config_entries.flow.async_progress()
     assert len(flows) == 1
     assert flows[0]["context"]["source"] == SOURCE_REAUTH
+
+
+async def test_setup_with_deauthorized_token(
+    hass: HomeAssistant, entry, setup_plex_server
+) -> None:
+    """Test setup with a deauthorized token."""
+    with patch(
+        "plexapi.server.PlexServer",
+        side_effect=plexapi.exceptions.BadRequest(const.INVALID_TOKEN_MESSAGE),
+    ):
+        entry.add_to_hass(hass)
+        assert not await hass.config_entries.async_setup(entry.entry_id)
+
+    flows = hass.config_entries.flow.async_progress()
+    assert len(flows) == 1
+    assert flows[0]["context"]["source"] == SOURCE_REAUTH