diff --git a/backend/open_webui/tools/builtin.py b/backend/open_webui/tools/builtin.py
index 08aed33aa0..fa8e02bc91 100644
--- a/backend/open_webui/tools/builtin.py
+++ b/backend/open_webui/tools/builtin.py
@@ -2857,12 +2857,56 @@ async def upload_file_to_terminal(
     try:
         from open_webui.models.files import Files
         from open_webui.storage.provider import Storage
+        from open_webui.utils.access_control import has_connection_access
         from open_webui.utils.access_control.files import has_access_to_file
 
         user_id = __user__.get('id')
         user_role = __user__.get('role', 'user')
 
-        # --- 1. Retrieve file and check access ---
+        # --- 1. Resolve terminal connection and build auth ---
+        cookies = {}
+        headers = {'X-User-Id': __user__.get('id', '')}
+
+        connections = __request__.app.state.config.TERMINAL_SERVER_CONNECTIONS or []
+        connection = next(
+            (c for c in connections if c.get('id') == terminal_id), None
+        )
+
+        if not connection:
+            return json.dumps({'error': f"Terminal connection '{terminal_id}' not found"})
+
+        if not await has_connection_access(UserModel(**__user__), connection):
+            return json.dumps({'error': 'Access denied to terminal server'})
+
+        terminal_url = connection.get('url', '').rstrip('/')
+
+        # Route through orchestrator policy endpoint if configured
+        policy_id = connection.get('policy_id')
+        if policy_id:
+            terminal_url = f'{terminal_url}/p/{policy_id}'
+
+        # Build auth headers/cookies matching resolve_terminal_tools pattern
+        auth_type = connection.get('auth_type', 'bearer')
+        if auth_type == 'bearer':
+            key = connection.get('key', '')
+            if key:
+                headers['Authorization'] = f'Bearer {key}'
+        elif auth_type == 'session':
+            cookies = __request__.cookies
+            if hasattr(__request__, 'state') and hasattr(__request__.state, 'token'):
+                headers['Authorization'] = f'Bearer {__request__.state.token.credentials}'
+        elif auth_type == 'system_oauth':
+            cookies = __request__.cookies
+            oauth_token = metadata.get('oauth_token') or {}
+            if oauth_token.get('access_token'):
+                headers['Authorization'] = f'Bearer {oauth_token["access_token"]}'
+        # auth_type == 'none': no Authorization header
+
+        chat_id = metadata.get('chat_id')
+        if chat_id:
+            headers['X-Session-Id'] = chat_id
+
+        # --- 2. Retrieve file and check access ---
         file_record = await Files.get_file_by_id(file_id)
         if not file_record:
             return json.dumps({'error': 'File not found'})
@@ -2880,65 +2924,6 @@ async def upload_file_to_terminal(
 
         local_path = Storage.get_file(file_record.path)
 
-        # --- 2. Resolve terminal connection and build auth ---
-        from open_webui.utils.access_control import has_connection_access
-
-        terminal_url = None
-        cookies = {}
-        headers = {'X-User-Id': __user__.get('id', '')}
-
-        # Try system terminal first (terminal_id is a connection ID)
-        connections = __request__.app.state.config.TERMINAL_SERVER_CONNECTIONS or []
-        connection = next(
-            (c for c in connections if c.get('id') == terminal_id), None
-        )
-
-        if connection:
-            if not await has_connection_access(UserModel(**__user__), connection):
-                return json.dumps({'error': 'Access denied to terminal server'})
-
-            terminal_url = connection.get('url', '').rstrip('/')
-
-            # Route through orchestrator policy endpoint if configured
-            policy_id = connection.get('policy_id')
-            if policy_id:
-                terminal_url = f'{terminal_url}/p/{policy_id}'
-
-            # Build auth headers/cookies matching resolve_terminal_tools pattern
-            auth_type = connection.get('auth_type', 'bearer')
-            if auth_type == 'bearer':
-                key = connection.get('key', '')
-                if key:
-                    headers['Authorization'] = f'Bearer {key}'
-            elif auth_type == 'session':
-                cookies = __request__.cookies
-                if hasattr(__request__, 'state') and hasattr(__request__.state, 'token'):
-                    headers['Authorization'] = f'Bearer {__request__.state.token.credentials}'
-            elif auth_type == 'system_oauth':
-                cookies = __request__.cookies
-                oauth_token = metadata.get('oauth_token') or {}
-                if oauth_token.get('access_token'):
-                    headers['Authorization'] = f'Bearer {oauth_token["access_token"]}'
-            # auth_type == 'none': no Authorization header
-        else:
-            # Try direct/user-configured terminal (terminal_id is the URL)
-            direct_tool_servers = metadata.get('tool_servers') or []
-            for ts in direct_tool_servers:
-                ts_url = (ts.get('url') or '').rstrip('/')
-                if ts_url and ts_url == terminal_id.rstrip('/'):
-                    terminal_url = ts_url
-                    key = ts.get('key', '')
-                    if key:
-                        headers['Authorization'] = f'Bearer {key}'
-                    break
-
-        if not terminal_url:
-            return json.dumps({'error': f"Terminal connection '{terminal_id}' could not be resolved"})
-
-        chat_id = metadata.get('chat_id')
-        if chat_id:
-            headers['X-Session-Id'] = chat_id
-
         # --- 3. Upload to terminal server ---
         import aiohttp
 
@@ -2975,7 +2960,7 @@ async def upload_file_to_terminal(
                     headers=headers,
                     cookies=cookies,
                 ) as response:
-                    if response.status != 200:
+                    if not (200 <= response.status < 300):
                         detail = (await response.text())[:500]
                         return json.dumps(
                             {'error': f'Upload failed (HTTP {response.status}): {detail}'}
@@ -2994,3 +2979,4 @@ async def upload_file_to_terminal(
     except Exception as e:
         log.exception(f'upload_file_to_terminal error: {e}')
         return json.dumps({'error': str(e)})
+