diff --git a/ui/desktop/src/components/settings/extensions/ExtensionsSection.tsx b/ui/desktop/src/components/settings/extensions/ExtensionsSection.tsx
index d1a72be95873..172f0794928f 100644
--- a/ui/desktop/src/components/settings/extensions/ExtensionsSection.tsx
+++ b/ui/desktop/src/components/settings/extensions/ExtensionsSection.tsx
@@ -48,11 +48,22 @@ export default function ExtensionsSection({
   const [showEnvVarsStateVar, setShowEnvVarsStateVar] = useState<boolean | undefined | null>(
     showEnvVars
   );
+  const [pendingActivationExtensions, setPendingActivationExtensions] = useState<Set<string>>(
+    new Set()
+  );
 
   // Update deep link state when props change
   useEffect(() => {
     setDeepLinkConfigStateVar(deepLinkConfig);
     setShowEnvVarsStateVar(showEnvVars);
+
+    if (deepLinkConfig && !showEnvVars) {
+      setPendingActivationExtensions((prev) => {
+        const updated = new Set(prev);
+        updated.add(deepLinkConfig.name);
+        return updated;
+      });
+    }
   }, [deepLinkConfig, showEnvVars]);
 
   // Process extensions from context - this automatically updates when extensionsList changes
@@ -102,6 +113,12 @@ export default function ExtensionsSection({
       sessionId: sessionId,
     });
 
+    setPendingActivationExtensions((prev) => {
+      const updated = new Set(prev);
+      updated.delete(extensionConfig.name);
+      return updated;
+    });
+
     await fetchExtensions();
     return true;
   };
@@ -122,8 +139,21 @@ export default function ExtensionsSection({
         extensionConfig: extensionConfig,
         sessionId: sessionId,
       });
+      setPendingActivationExtensions((prev) => {
+        const updated = new Set(prev);
+        updated.delete(extensionConfig.name);
+        return updated;
+      });
     } catch (error) {
       console.error('Failed to activate extension:', error);
+      // If activation fails, mark as pending if it's enabled in config
+      if (formData.enabled) {
+        setPendingActivationExtensions((prev) => {
+          const updated = new Set(prev);
+          updated.add(extensionConfig.name);
+          return updated;
+        });
+      }
     } finally {
       await fetchExtensions();
       if (onModalClose) {
@@ -202,6 +232,7 @@ export default function ExtensionsSection({
           onConfigure={handleConfigureClick}
           disableConfiguration={disableConfiguration}
           searchTerm={searchTerm}
+          pendingActivationExtensions={pendingActivationExtensions}
         />
 
         {!hideButtons && (
diff --git a/ui/desktop/src/components/settings/extensions/subcomponents/ExtensionItem.tsx b/ui/desktop/src/components/settings/extensions/subcomponents/ExtensionItem.tsx
index 872142dfbce9..f677260332eb 100644
--- a/ui/desktop/src/components/settings/extensions/subcomponents/ExtensionItem.tsx
+++ b/ui/desktop/src/components/settings/extensions/subcomponents/ExtensionItem.tsx
@@ -11,6 +11,7 @@ interface ExtensionItemProps {
   onToggle: (extension: FixedExtensionEntry) => Promise<boolean | void> | void;
   onConfigure?: (extension: FixedExtensionEntry) => void;
   isStatic?: boolean; // to not allow users to edit configuration
+  isPendingActivation?: boolean;
 }
 
 export default function ExtensionItem({
@@ -18,6 +19,7 @@ export default function ExtensionItem({
   onToggle,
   onConfigure,
   isStatic,
+  isPendingActivation = false,
 }: ExtensionItemProps) {
   // Add local state to track the visual toggle state
   const [visuallyEnabled, setVisuallyEnabled] = useState(extension.enabled);
@@ -79,7 +81,17 @@ export default function ExtensionItem({
       onClick={() => handleToggle(extension)}
     >
       <CardHeader>
-        <CardTitle className="">{getFriendlyTitle(extension)}</CardTitle>
+        <CardTitle className="flex items-center gap-2">
+          {getFriendlyTitle(extension)}
+          {isPendingActivation && (
+            <span
+              className="inline-flex items-center px-2 py-0.5 rounded text-xs font-medium bg-amber-100 text-amber-800 dark:bg-amber-900/30 dark:text-amber-400 border border-amber-300 dark:border-amber-700"
+              title="Extension will be activated when you start a new chat session"
+            >
+              Pending
+            </span>
+          )}
+        </CardTitle>
 
         <CardAction onClick={(e) => e.stopPropagation()}>
           <div className="flex items-center justify-end gap-2">
diff --git a/ui/desktop/src/components/settings/extensions/subcomponents/ExtensionList.tsx b/ui/desktop/src/components/settings/extensions/subcomponents/ExtensionList.tsx
index a39137076e2f..a2ab0b121fbf 100644
--- a/ui/desktop/src/components/settings/extensions/subcomponents/ExtensionList.tsx
+++ b/ui/desktop/src/components/settings/extensions/subcomponents/ExtensionList.tsx
@@ -11,6 +11,7 @@ interface ExtensionListProps {
   isStatic?: boolean;
   disableConfiguration?: boolean;
   searchTerm?: string;
+  pendingActivationExtensions?: Set<string>;
 }
 
 export default function ExtensionList({
@@ -20,6 +21,7 @@ export default function ExtensionList({
   isStatic,
   disableConfiguration: _disableConfiguration,
   searchTerm = '',
+  pendingActivationExtensions = new Set(),
 }: ExtensionListProps) {
   const matchesSearch = (extension: FixedExtensionEntry): boolean => {
     if (!searchTerm) return true;
@@ -63,6 +65,7 @@ export default function ExtensionList({
                 onToggle={onToggle}
                 onConfigure={onConfigure}
                 isStatic={isStatic}
+                isPendingActivation={pendingActivationExtensions.has(extension.name)}
               />
             ))}
           </div>