diff --git a/lib/constants.py b/lib/constants.py
index 150ca13..3c61920 100644
--- a/lib/constants.py
+++ b/lib/constants.py
@@ -24,7 +24,8 @@
 RBX_PACKAGE_ID_PROPERTY_NAME = "Roblox Package ID"
 ASSET_DESCRIPTION = "Uploaded from Blender"
 ERROR_MESSAGES = {
-    "TIMED_OUT": "Timed Out",
+    "UPLOAD_TIMED_OUT": "Upload Timed Out",
+    "OPERATION_TIMED_OUT": "Operation Timed Out",
     "INVALID_RESPONSE": "Invalid Response",
     "ADD_ON_ERROR": "Add-on Error",
 }
diff --git a/lib/upload_operator.py b/lib/upload_operator.py
index 2bf85e9..82465ea 100644
--- a/lib/upload_operator.py
+++ b/lib/upload_operator.py
@@ -237,6 +237,7 @@ def upload_task_complete(task, window_manager, area, target_object, temporary_di
         property and cleaning up from the operation."""
         from . import status_indicators, constants
         import openapi_client
+        import asyncio
 
         try:
             operation = task.result()
@@ -248,7 +249,7 @@ def upload_task_complete(task, window_manager, area, target_object, temporary_di
             elif not operation.done:
                 # Timeout while polling for upload job to finish. It may yet finish or fail, but we stopped checking.
                 status_indicators.set_status(
-                    window_manager, area, target_object, constants.ERROR_MESSAGES["TIMED_OUT"], "ERROR"
+                    window_manager, area, target_object, constants.ERROR_MESSAGES["OPERATION_TIMED_OUT"], "ERROR"
                 )
             elif operation.response:
                 # Success
@@ -266,7 +267,11 @@ def upload_task_complete(task, window_manager, area, target_object, temporary_di
                     window_manager, area, target_object, constants.ERROR_MESSAGES["INVALID_RESPONSE"], "ERROR"
                 )
                 print(f"Upload failed, invalid response:\n{operation}")
-
+        except asyncio.exceptions.TimeoutError as exception:
+            # Timeout while waiting for initial upload to return an operation ID. It may yet finish or fail, but we stopped waiting.
+            status_indicators.set_status(
+                window_manager, area, target_object, constants.ERROR_MESSAGES["UPLOAD_TIMED_OUT"], "ERROR"
+            )
         except openapi_client.rest.ApiException as exception:
             traceback.print_exception(exception)
             from .extract_exception_message import extract_exception_message