diff --git a/src/McpServer/autopilot-monitor-mcp/src/access-guard.ts b/src/McpServer/autopilot-monitor-mcp/src/access-guard.ts
index bd9f4516..3b7f4d54 100644
--- a/src/McpServer/autopilot-monitor-mcp/src/access-guard.ts
+++ b/src/McpServer/autopilot-monitor-mcp/src/access-guard.ts
@@ -12,6 +12,16 @@ import { extractTokenClaims, isTokenExpired } from './auth.js';
 import { setCurrentToken } from './client.js';
 
 const BASE_URL = process.env.AUTOPILOT_API_URL ?? 'https://autopilotmonitor-api.azurewebsites.net';
+
+/**
+ * Derives the public base URL for the WWW-Authenticate header.
+ */
+function getPublicBaseUrl(req: Request): string {
+  if (process.env.MCP_PUBLIC_URL) return process.env.MCP_PUBLIC_URL;
+  const proto = (req.headers['x-forwarded-proto'] as string) ?? req.protocol;
+  const host = (req.headers['x-forwarded-host'] as string) ?? req.headers.host;
+  return `${proto}://${host}`;
+}
 const RATE_LIMIT = parseInt(process.env.MCP_RATE_LIMIT_PER_MINUTE ?? '60', 10);
 const ACCESS_CACHE_TTL_MS = 5 * 60 * 1000; // 5 minutes
 
@@ -100,8 +110,12 @@ function isRateLimited(upn: string): boolean {
 // --- Express middleware ---
 
 export function accessGuard(req: Request, res: Response, next: NextFunction): void {
+  const baseUrl = getPublicBaseUrl(req);
+  const resourceMetadataUrl = `${baseUrl}/.well-known/oauth-protected-resource`;
+
   const authHeader = req.headers.authorization;
   if (!authHeader?.startsWith('Bearer ')) {
+    res.setHeader('WWW-Authenticate', `Bearer resource_metadata="${resourceMetadataUrl}"`);
     res.status(401).json({ error: 'Missing or invalid Authorization header' });
     return;
   }
@@ -109,11 +123,13 @@ export function accessGuard(req: Request, res: Response, next: NextFunction): vo
   const token = authHeader.slice(7);
   const claims = extractTokenClaims(token);
   if (!claims || !claims.upn) {
+    res.setHeader('WWW-Authenticate', `Bearer resource_metadata="${resourceMetadataUrl}", error="invalid_token"`);
     res.status(401).json({ error: 'Invalid token: missing required claims' });
     return;
   }
 
   if (isTokenExpired(claims)) {
+    res.setHeader('WWW-Authenticate', `Bearer resource_metadata="${resourceMetadataUrl}", error="invalid_token"`);
     res.status(401).json({ error: 'Token expired' });
     return;
   }
diff --git a/src/McpServer/autopilot-monitor-mcp/src/oauth.ts b/src/McpServer/autopilot-monitor-mcp/src/oauth.ts
index c74382ef..80bc56e4 100644
--- a/src/McpServer/autopilot-monitor-mcp/src/oauth.ts
+++ b/src/McpServer/autopilot-monitor-mcp/src/oauth.ts
@@ -6,10 +6,15 @@
  * endpoints, which redirect to/from Entra ID.
  *
  * Flow:
- *   1. Claude Code → GET /oauth/authorize → 302 to Entra ID /authorize
- *   2. User authenticates at Entra ID
- *   3. Entra ID → GET /oauth/callback → 302 back to Claude Code with code
- *   4. Claude Code → POST /oauth/token → proxied to Entra ID /token
+ *   1. Claude Code → POST /mcp → 401 (with WWW-Authenticate header)
+ *   2. Claude Code → GET /.well-known/oauth-protected-resource → discovers auth server (RFC 9728)
+ *   3. Claude Code → GET /.well-known/oauth-authorization-server → discovers endpoints (RFC 8414)
+ *   4. Claude Code → POST /oauth/register → dynamic client registration (RFC 7591)
+ *   5. Claude Code → GET /oauth/authorize → 302 to Entra ID /authorize
+ *   6. User authenticates at Entra ID
+ *   7. Entra ID → GET /oauth/callback → 302 back to Claude Code with code
+ *   8. Claude Code → POST /oauth/token → proxied to Entra ID /token
+ *   9. Claude Code → POST /mcp (with Bearer token) → MCP session established
  */
 import { Router } from 'express';
 import crypto from 'node:crypto';
@@ -42,6 +47,19 @@ function getPublicBaseUrl(req: import('express').Request): string {
 export function createOAuthRouter(): Router {
   const router = Router();
 
+  // --- Protected Resource Metadata (RFC 9728) ---
+  // This is the FIRST endpoint Claude Code fetches after receiving a 401.
+  // It tells the client where the authorization server lives.
+  router.get('/.well-known/oauth-protected-resource', (req, res) => {
+    const baseUrl = getPublicBaseUrl(req);
+    res.json({
+      resource: baseUrl,
+      authorization_servers: [baseUrl],
+      bearer_methods_supported: ['header'],
+      scopes_supported: ['openid', 'profile', 'offline_access', `api://${CLIENT_ID}/access_as_user`],
+    });
+  });
+
   // --- OAuth Authorization Server Metadata (RFC 8414) ---
   router.get('/.well-known/oauth-authorization-server', (req, res) => {
     const baseUrl = getPublicBaseUrl(req);