diff --git a/surfsense_backend/app/tasks/chat/stream_new_chat.py b/surfsense_backend/app/tasks/chat/stream_new_chat.py
index 1a56547ca..233b45396 100644
--- a/surfsense_backend/app/tasks/chat/stream_new_chat.py
+++ b/surfsense_backend/app/tasks/chat/stream_new_chat.py
@@ -1542,7 +1542,7 @@ async def stream_new_chat(
                     llm_config_id,
                 )
                 yield streaming_service.format_error(
-                    "Premium token quota exceeded for this pinned model. Select a free model or re-select Auto (Fastest) to repin."
+                    "Premium tokens exhausted. Buy more tokens to continue with this model, or switch to a free model."
                 )
                 yield streaming_service.format_done()
                 return
@@ -2263,7 +2263,7 @@ async def stream_resume_chat(
                     llm_config_id,
                 )
                 yield streaming_service.format_error(
-                    "Premium token quota exceeded for this pinned model. Select a free model or re-select Auto (Fastest) to repin."
+                    "Premium tokens exhausted. Buy more tokens to continue with this model, or switch to a free model."
                 )
                 yield streaming_service.format_done()
                 return
diff --git a/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx b/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx
index a5461e17f..05621419d 100644
--- a/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx
+++ b/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx
@@ -201,17 +201,16 @@ const BASE_TOOLS_WITH_UI = new Set([
 	// "write_todos", // Disabled for now
 ]);
 
-const PINNED_PREMIUM_QUOTA_MESSAGE = "Premium token quota exceeded for this pinned model.";
-
 function getPinnedPremiumQuotaErrorMessage(error: unknown): string | null {
 	if (!(error instanceof Error)) return null;
-	if (!error.message.toLowerCase().includes("premium token quota exceeded")) {
+	const normalized = error.message.toLowerCase();
+	if (
+		!normalized.includes("premium tokens exhausted")
+		&& !normalized.includes("premium token quota exceeded")
+	) {
 		return null;
 	}
-	if (!error.message.toLowerCase().includes("pinned model")) {
-		return null;
-	}
-	return error.message || PINNED_PREMIUM_QUOTA_MESSAGE;
+	return error.message;
 }
 
 export default function NewChatPage() {
@@ -980,7 +979,6 @@ export default function NewChatPage() {
 						threadId: currentThreadId,
 						message: premiumQuotaAlertMessage,
 					});
-					toast.error(PINNED_PREMIUM_QUOTA_MESSAGE);
 				} else {
 					toast.error("Failed to get response. Please try again.");
 				}
@@ -1290,7 +1288,6 @@ export default function NewChatPage() {
 						threadId: resumeThreadId,
 						message: premiumQuotaAlertMessage,
 					});
-					toast.error(PINNED_PREMIUM_QUOTA_MESSAGE);
 				} else {
 					toast.error("Failed to resume. Please try again.");
 				}
@@ -1638,7 +1635,6 @@ export default function NewChatPage() {
 						threadId,
 						message: premiumQuotaAlertMessage,
 					});
-					toast.error(PINNED_PREMIUM_QUOTA_MESSAGE);
 				} else {
 					toast.error("Failed to regenerate response. Please try again.");
 				}
diff --git a/surfsense_web/components/assistant-ui/thread.tsx b/surfsense_web/components/assistant-ui/thread.tsx
index 06f25f5fb..cb063fac3 100644
--- a/surfsense_web/components/assistant-ui/thread.tsx
+++ b/surfsense_web/components/assistant-ui/thread.tsx
@@ -161,16 +161,15 @@ const PremiumQuotaPinnedAlert: FC = () => {
 	if (!alert) return null;
 
 	return (
-		<div className="mx-2 rounded-2xl border border-amber-300/40 bg-amber-500/10 px-4 py-3 text-amber-50 shadow-lg backdrop-blur-sm">
+		<div className="mx-0 bg-amber-500/10 px-3 py-2 text-amber-100">
 			<div className="flex items-start gap-2">
 				<AlertCircle className="mt-0.5 size-4 shrink-0 text-amber-300" />
 				<div className="min-w-0 flex-1">
-					<p className="text-sm font-medium">Premium quota exhausted</p>
-					<p className="mt-1 text-xs text-amber-100/90">{alert.message}</p>
+					<p className="text-sm">{alert.message}</p>
 				</div>
 				<button
 					type="button"
-					className="inline-flex size-6 items-center justify-center rounded-md text-amber-200 transition-colors hover:bg-amber-200/20 hover:text-amber-50"
+					className="inline-flex size-6 items-center justify-center text-amber-200 transition-colors hover:text-amber-50"
 					aria-label="Dismiss premium quota alert"
 					onClick={() => clearPremiumAlertForThread(currentThreadId)}
 				>