@@ -1,18 +1,26 @@
 import type { KiloNotification } from '@/lib/notifications';
 import { generateUserNotifications } from '@/lib/notifications';
 import { getUserFromAuth } from '@/lib/user/server';
-import { NextResponse } from 'next/server';
+import { isLegacyKiloExtensionNotificationsUserAgent } from '@/lib/userAgent';
+import { type NextRequest, NextResponse } from 'next/server';
 
-export async function GET(): Promise<
-  NextResponse<{ error: string } | { notifications: KiloNotification[] }>
-> {
+export async function GET(
+  request: NextRequest
+): Promise<NextResponse<{ error: string } | { notifications: KiloNotification[] }>> {
   const { user, authFailedResponse } = await getUserFromAuth({
     adminOnly: false,
   });
 
   if (authFailedResponse) return authFailedResponse;
 
-  const notifications = await generateUserNotifications(user);
+  // The legacy extension calls this endpoint with axios (User-Agent: axios/<version>),
+  // while the current extension/CLI use the shared Kilo gateway headers. Detecting the
+  // axios User-Agent lets us target the legacy-extension end-of-life notice precisely.
+  const isLegacyExtension = isLegacyKiloExtensionNotificationsUserAgent(
+    request.headers.get('user-agent')
+  );
+
+  const notifications = await generateUserNotifications(user, { isLegacyExtension });
 
   return NextResponse.json({ notifications });
 }
@@ -0,0 +1,15 @@
+import { describe, test, expect } from '@jest/globals';
+import { passesLegacyExtensionGate } from './notifications';
+
+describe('passesLegacyExtensionGate', () => {
+  test('always shows notifications not gated to the legacy extension', () => {
+    expect(passesLegacyExtensionGate({}, false)).toBe(true);
+    expect(passesLegacyExtensionGate({}, true)).toBe(true);
+    expect(passesLegacyExtensionGate({ showOnlyOnLegacyExtension: false }, false)).toBe(true);
+  });
+
+  test('shows legacy-gated notifications only to the legacy extension', () => {
+    expect(passesLegacyExtensionGate({ showOnlyOnLegacyExtension: true }, true)).toBe(true);
+    expect(passesLegacyExtensionGate({ showOnlyOnLegacyExtension: true }, false)).toBe(false);
+  });
+});
@@ -33,11 +33,39 @@ export type KiloNotification = {
   showIn?: ('extension' | 'extension-native' | 'cli')[];
   // ISO 8601 timestamp after which this notification should no longer be shown
   expiresAt?: string;
+  // When true, only show to the legacy ("Roo-based") Kilo Code extension, identified by
+  // its axios User-Agent. Used to target end-of-life notices at legacy-extension users.
+  showOnlyOnLegacyExtension?: boolean;
 };
 
+/**
+ * Decide whether a legacy-targeted notification should be shown to a client.
+ * Notifications flagged showOnlyOnLegacyExtension are shown only when the request
+ * came from the legacy extension (detected via its axios User-Agent).
+ */
+export function passesLegacyExtensionGate(
+  notification: Pick<KiloNotification, 'showOnlyOnLegacyExtension'>,
+  isLegacyExtension: boolean
+): boolean {
+  if (!notification.showOnlyOnLegacyExtension) return true;
+  return isLegacyExtension;
+}
+
 const normalUnconditionalNotifications: KiloNotification[] = [
   //If you need to check or personalize the notification, see examples at the bottom of this file
   //if you just want a simple straightforward global message, add it here.
+  {
+    id: 'legacy-upgrade-june-2026',
+    title: 'Kilo Code 5.x: End of Life July 31, 2026',
+    message:
+      'Kilo Code extension version 5.x reaches end of life on July 31, 2026. After that date, it will no longer receive updates, bug fixes, or security patches. Upgrade to the latest version for continued support.',
+    action: {
+      actionText: 'See End of Life Notice',
+      actionURL: 'https://github.com/Kilo-Org/kilocode-legacy#legacy-ide-extensions-end-of-life',
+    },
+    showIn: ['extension'],
+    showOnlyOnLegacyExtension: true,
+  },
   {
     id: 'star-giveaway-june-2026',
     title: 'GitHub Star Giveaway',
@@ -113,7 +141,10 @@ const normalUnconditionalNotifications: KiloNotification[] = [
   },
 ];
 
-export async function generateUserNotifications(user: User): Promise<KiloNotification[]> {
+export async function generateUserNotifications(
+  user: User,
+  { isLegacyExtension = false }: { isLegacyExtension?: boolean } = {}
+): Promise<KiloNotification[]> {
   // Pre-fetch shared data once to avoid duplicate DB queries across generators.
   // This eliminates ~5 redundant queries per request (2× userHasOrganizations,
   // 3× getUserOrganizationsWithSeats, 2× getBalanceForUser → 1+1 queries).
@@ -147,9 +178,11 @@ export async function generateUserNotifications(user: User): Promise<KiloNotific
   ).flat();
 
   const now = new Date();
-  return [...resolvedConditionalNotifications, ...normalUnconditionalNotifications].filter(
-    n => !n.expiresAt || new Date(n.expiresAt) > now
-  );
+  return [...resolvedConditionalNotifications, ...normalUnconditionalNotifications].filter(n => {
+    if (n.expiresAt && new Date(n.expiresAt) <= now) return false;
+    if (!passesLegacyExtensionGate(n, isLegacyExtension)) return false;
+    return true;
+  });
 }
 
 async function generateLowCreditNotification(
 
@@ -1,5 +1,9 @@
 import { describe, test, expect } from '@jest/globals';
-import { getKiloCodeVersionNumber, getXKiloCodeVersionNumber } from './userAgent';
+import {
+  getKiloCodeVersionNumber,
+  getXKiloCodeVersionNumber,
+  isLegacyKiloExtensionNotificationsUserAgent,
+} from './userAgent';
 
 describe('getKiloCodeVersionNumber', () => {
   test('returns undefined for non-Kilo-Code user agents', () => {
@@ -51,3 +55,21 @@ describe('getKiloCodeVersionNumber', () => {
     expect(getXKiloCodeVersionNumber('4.65.3-alpha.1 extra-info')).toBeCloseTo(4.065003, 10);
   });
 });
+
+describe('isLegacyKiloExtensionNotificationsUserAgent', () => {
+  test('matches the legacy extension axios User-Agent', () => {
+    expect(isLegacyKiloExtensionNotificationsUserAgent('axios/1.7.2')).toBe(true);
+    expect(isLegacyKiloExtensionNotificationsUserAgent('axios/0.27.2')).toBe(true);
+  });
+
+  test('does not match current extension, CLI, bot, or missing User-Agents', () => {
+    expect(isLegacyKiloExtensionNotificationsUserAgent(null)).toBe(false);
+    expect(isLegacyKiloExtensionNotificationsUserAgent(undefined)).toBe(false);
+    expect(isLegacyKiloExtensionNotificationsUserAgent('')).toBe(false);
+    expect(isLegacyKiloExtensionNotificationsUserAgent('opencode-kilo-provider/7.1.0')).toBe(false);
+    expect(isLegacyKiloExtensionNotificationsUserAgent('opencode-kilo-provider')).toBe(false);
+    expect(isLegacyKiloExtensionNotificationsUserAgent('Kilo-Code/5.1.0')).toBe(false);
+    expect(isLegacyKiloExtensionNotificationsUserAgent('Mozilla/5.0 Test Browser')).toBe(false);
+    expect(isLegacyKiloExtensionNotificationsUserAgent('my-axios/1.0.0')).toBe(false);
+  });
+});
@@ -3,6 +3,17 @@ export function getKiloCodeVersionNumber(userAgent: string | null | undefined):
   if (!userAgent || !userAgent.startsWith(userAgentPrefix)) return undefined;
   return getXKiloCodeVersionNumber(userAgent.slice(userAgentPrefix.length));
 }
+
+// The legacy ("Roo-based") Kilo Code extension fetches notifications with axios from
+// the Node extension host, which sends `User-Agent: axios/<version>`. The current
+// extension and CLI use the shared Kilo gateway headers instead (`opencode-kilo-provider/...`).
+// This heuristic is only meaningful for the notifications endpoint: axios is a generic
+// HTTP client (also used for LLM calls), so it is not a general "is legacy extension" signal.
+export function isLegacyKiloExtensionNotificationsUserAgent(
+  userAgent: string | null | undefined
+): boolean {
+  return !!userAgent && userAgent.startsWith('axios/');
+}
 export function getXKiloCodeVersionNumber(
   userAgent: string | null | undefined
 ): number | undefined {