diff --git a/homeassistant/components/media_player/plex.py b/homeassistant/components/media_player/plex.py
index a36eb08f851..f4c69ba1fe6 100644
--- a/homeassistant/components/media_player/plex.py
+++ b/homeassistant/components/media_player/plex.py
@@ -170,9 +170,9 @@ def setup_plexserver(
         except plexapi.exceptions.BadRequest:
             _LOGGER.exception("Error listing plex devices")
             return
-        except OSError:
-            _LOGGER.error("Could not connect to plex server at http://%s",
-                          host)
+        except requests.exceptions.RequestException as ex:
+            _LOGGER.error("Could not connect to plex server at http://%s (%s)",
+                          host, ex)
             return
 
         new_plex_clients = []
@@ -219,6 +219,10 @@ def setup_plexserver(
         except plexapi.exceptions.BadRequest:
             _LOGGER.exception("Error listing plex sessions")
             return
+        except requests.exceptions.RequestException as ex:
+            _LOGGER.error("Could not connect to plex server at http://%s (%s)",
+                          host, ex)
+            return
 
         plex_sessions.clear()
         for session in sessions: