diff --git a/surfsense_backend/app/agents/new_chat/tools/google_drive/trash_file.py b/surfsense_backend/app/agents/new_chat/tools/google_drive/trash_file.py
index 56b43e265..600aae983 100644
--- a/surfsense_backend/app/agents/new_chat/tools/google_drive/trash_file.py
+++ b/surfsense_backend/app/agents/new_chat/tools/google_drive/trash_file.py
@@ -86,7 +86,7 @@ def create_delete_google_drive_file_tool(
                 }
 
             logger.info(
-                f"Requesting approval for trashing Google Drive file: '{file_name}' (file_id={file_id}, delete_from_kb={delete_from_kb})"
+                f"Requesting approval for deleting Google Drive file: '{file_name}' (file_id={file_id}, delete_from_kb={delete_from_kb})"
             )
             approval = interrupt(
                 {
@@ -157,7 +157,7 @@ def create_delete_google_drive_file_tool(
                 }
 
             logger.info(
-                f"Trashing Google Drive file: file_id='{final_file_id}', connector={final_connector_id}"
+                f"Deleting Google Drive file: file_id='{final_file_id}', connector={final_connector_id}"
             )
             client = GoogleDriveClient(session=db_session, connector_id=connector.id)
             try:
@@ -174,7 +174,7 @@ def create_delete_google_drive_file_tool(
                     }
                 raise
 
-            logger.info(f"Google Drive file trashed: file_id={final_file_id}")
+            logger.info(f"Google Drive file deleted (moved to trash): file_id={final_file_id}")
 
             trash_result: dict[str, Any] = {
                 "status": "success",
@@ -219,7 +219,7 @@ def create_delete_google_drive_file_tool(
             if isinstance(e, GraphInterrupt):
                 raise
 
-            logger.error(f"Error trashing Google Drive file: {e}", exc_info=True)
+            logger.error(f"Error deleting Google Drive file: {e}", exc_info=True)
             return {
                 "status": "error",
                 "message": "Something went wrong while trashing the file. Please try again.",
diff --git a/surfsense_backend/app/agents/new_chat/tools/registry.py b/surfsense_backend/app/agents/new_chat/tools/registry.py
index 565de01ab..01342e920 100644
--- a/surfsense_backend/app/agents/new_chat/tools/registry.py
+++ b/surfsense_backend/app/agents/new_chat/tools/registry.py
@@ -297,7 +297,7 @@ BUILTIN_TOOLS: list[ToolDefinition] = [
         requires=["db_session", "search_space_id", "user_id"],
     ),
     # =========================================================================
-    # GOOGLE DRIVE TOOLS - create files, trash files
+    # GOOGLE DRIVE TOOLS - create files, delete files
     # =========================================================================
     ToolDefinition(
         name="create_google_drive_file",
diff --git a/surfsense_web/components/tool-ui/google-drive/create-file.tsx b/surfsense_web/components/tool-ui/google-drive/create-file.tsx
index 548347587..b56abf18b 100644
--- a/surfsense_web/components/tool-ui/google-drive/create-file.tsx
+++ b/surfsense_web/components/tool-ui/google-drive/create-file.tsx
@@ -12,6 +12,7 @@ import {
 } from "lucide-react";
 import { useParams } from "next/navigation";
 import { useMemo, useState } from "react";
+import { toast } from "sonner";
 import { Button } from "@/components/ui/button";
 import { Input } from "@/components/ui/input";
 import {
@@ -426,10 +427,17 @@ function InsufficientPermissionsCard({ result }: { result: InsufficientPermissio
 			url.searchParams.set("space_id", searchSpaceId);
 			url.searchParams.set("return_url", window.location.pathname);
 			const response = await authenticatedFetch(url.toString());
+			if (!response.ok) {
+				const data = await response.json().catch(() => ({}));
+				toast.error(data.detail ?? "Failed to initiate re-authentication. Please try again.");
+				return;
+			}
 			const data = await response.json();
 			if (data.auth_url) {
 				window.location.href = data.auth_url;
 			}
+		} catch {
+			toast.error("Failed to initiate re-authentication. Please try again.");
 		} finally {
 			setLoading(false);
 		}
diff --git a/surfsense_web/components/tool-ui/google-drive/trash-file.tsx b/surfsense_web/components/tool-ui/google-drive/trash-file.tsx
index 0c1ca981c..ee4c94d51 100644
--- a/surfsense_web/components/tool-ui/google-drive/trash-file.tsx
+++ b/surfsense_web/components/tool-ui/google-drive/trash-file.tsx
@@ -12,6 +12,7 @@ import {
 } from "lucide-react";
 import { useParams } from "next/navigation";
 import { useState } from "react";
+import { toast } from "sonner";
 import { Button } from "@/components/ui/button";
 import { authenticatedFetch } from "@/lib/auth-utils";
 
@@ -334,10 +335,17 @@ function InsufficientPermissionsCard({ result }: { result: InsufficientPermissio
 			url.searchParams.set("space_id", searchSpaceId);
 			url.searchParams.set("return_url", window.location.pathname);
 			const response = await authenticatedFetch(url.toString());
+			if (!response.ok) {
+				const data = await response.json().catch(() => ({}));
+				toast.error(data.detail ?? "Failed to initiate re-authentication. Please try again.");
+				return;
+			}
 			const data = await response.json();
 			if (data.auth_url) {
 				window.location.href = data.auth_url;
 			}
+		} catch {
+			toast.error("Failed to initiate re-authentication. Please try again.");
 		} finally {
 			setLoading(false);
 		}