diff --git a/src/__tests__/oauth-e2e.test.ts b/src/__tests__/oauth-e2e.test.ts
index 3331147..a41623c 100644
--- a/src/__tests__/oauth-e2e.test.ts
+++ b/src/__tests__/oauth-e2e.test.ts
@@ -383,7 +383,14 @@ describe("OAuth 2.1 end-to-end ceremonial flow", () => {
     expect(res.status).toBe(401);
     const www = res.headers.get("www-authenticate");
     expect(www).toContain('Bearer realm="mcp"');
+    // RFC 9728: discovery URL advertised on WWW-Authenticate so the client
+    // can fetch the protected-resource metadata document. Per RFC 6750 §3.1,
+    // the `error="invalid_token"` attribute MUST also be in the header (it
+    // is additionally returned in the JSON response body).
+    expect(www).toContain("resource_metadata=");
     expect(www).toContain('error="invalid_token"');
+    const body = (await res.json()) as { error?: string };
+    expect(body.error).toBe("invalid_token");
   });
 
   // ──────────────────────────────────────────────────────────────────
diff --git a/src/__tests__/oauth-handlers.test.ts b/src/__tests__/oauth-handlers.test.ts
index 9822566..20942f9 100644
--- a/src/__tests__/oauth-handlers.test.ts
+++ b/src/__tests__/oauth-handlers.test.ts
@@ -1511,6 +1511,15 @@ describe("bearerMiddleware", () => {
       "WWW-Authenticate",
       expect.stringContaining('Bearer realm="mcp"'),
     );
+    // RFC 9728: `WWW-Authenticate` advertises `resource_metadata=` so
+    // clients can discover the protected-resource document. Per RFC 6750
+    // §3.1, when a Bearer token is present-but-invalid the `error=`
+    // attribute MUST also be in the `WWW-Authenticate` header (it is
+    // additionally returned in the JSON body).
+    expect(res.setHeader).toHaveBeenCalledWith(
+      "WWW-Authenticate",
+      expect.stringContaining("resource_metadata="),
+    );
     expect(res.setHeader).toHaveBeenCalledWith(
       "WWW-Authenticate",
       expect.stringContaining('error="invalid_token"'),
@@ -1577,6 +1586,128 @@ describe("bearerMiddleware", () => {
     expect(res.status).toHaveBeenCalledWith(401);
     expect(next).not.toHaveBeenCalled();
   });
+
+  // ──────────────────────────────────────────────────────────────────────
+  // RFC 9728 — every Bearer 401 must include `resource_metadata=` on
+  // `WWW-Authenticate` so clients can discover the protected-resource
+  // metadata document. The helper at handlers.ts:626 constructs the URL
+  // from `originOf(req)` + "/.well-known/oauth-protected-resource"; tests
+  // mirror that construction to detect drift.
+  // ──────────────────────────────────────────────────────────────────────
+  describe("RFC 9728 resource_metadata discovery on 401", () => {
+    const expectedResourceMetadata =
+      "https://mcp.example.com/.well-known/oauth-protected-resource";
+
+    function assertDiscoveryHeader(
+      res: ReturnType<typeof mockRes>,
+      next: ReturnType<typeof vi.fn>,
+    ): void {
+      expect(res.status).toHaveBeenCalledWith(401);
+      expect(next).not.toHaveBeenCalled();
+      expect(res.setHeader).toHaveBeenCalledWith(
+        "WWW-Authenticate",
+        expect.stringContaining("Bearer"),
+      );
+      expect(res.setHeader).toHaveBeenCalledWith(
+        "WWW-Authenticate",
+        expect.stringContaining(
+          `resource_metadata="${expectedResourceMetadata}"`,
+        ),
+      );
+      // RFC 6750 §3.1 — when a Bearer token is present-but-invalid the
+      // `error=` attribute MUST appear in `WWW-Authenticate`.
+      expect(res.setHeader).toHaveBeenCalledWith(
+        "WWW-Authenticate",
+        expect.stringContaining('error="invalid_token"'),
+      );
+    }
+
+    it("empty Bearer token → 401 + resource_metadata", () => {
+      const req = mockReq({
+        headers: {
+          host: "mcp.example.com",
+          "x-forwarded-proto": "https",
+          authorization: "Bearer ",
+        },
+      });
+      const res = mockRes();
+      const next = vi.fn();
+      bearerMiddleware(req as never, res as never, next);
+      assertDiscoveryHeader(res, next);
+    });
+
+    it("invalid signature → 401 + resource_metadata", () => {
+      const now = Math.floor(Date.now() / 1000);
+      const token = signJWT(
+        {
+          sub: "x",
+          aud: "https://mcp.example.com",
+          iat: now,
+          exp: now + 3600,
+        },
+        "wrong-secret-xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx",
+      );
+      const req = mockReq({
+        headers: {
+          host: "mcp.example.com",
+          "x-forwarded-proto": "https",
+          authorization: `Bearer ${token}`,
+        },
+      });
+      const res = mockRes();
+      const next = vi.fn();
+      bearerMiddleware(req as never, res as never, next);
+      assertDiscoveryHeader(res, next);
+    });
+
+    it("expired token → 401 + resource_metadata", () => {
+      const now = Math.floor(Date.now() / 1000);
+      const token = signJWT(
+        {
+          sub: "x",
+          aud: "https://mcp.example.com",
+          iat: now - 7200,
+          exp: now - 3600,
+        },
+        "a".repeat(64),
+      );
+      const req = mockReq({
+        headers: {
+          host: "mcp.example.com",
+          "x-forwarded-proto": "https",
+          authorization: `Bearer ${token}`,
+        },
+      });
+      const res = mockRes();
+      const next = vi.fn();
+      bearerMiddleware(req as never, res as never, next);
+      assertDiscoveryHeader(res, next);
+    });
+
+    it("aud mismatch → 401 + resource_metadata", () => {
+      const now = Math.floor(Date.now() / 1000);
+      const token = signJWT(
+        {
+          sub: "x",
+          aud: "https://other.example",
+          iat: now,
+          exp: now + 3600,
+        },
+        "a".repeat(64),
+      );
+      const req = mockReq({
+        headers: {
+          host: "mcp.example.com",
+          "x-forwarded-proto": "https",
+          authorization: `Bearer ${token}`,
+        },
+      });
+      const res = mockRes();
+      const next = vi.fn();
+      bearerMiddleware(req as never, res as never, next);
+      assertDiscoveryHeader(res, next);
+    });
+  });
 });
 
 // Keep module-level state from leaking across files
diff --git a/src/oauth/handlers.ts b/src/oauth/handlers.ts
index 888c89a..76986f1 100644
--- a/src/oauth/handlers.ts
+++ b/src/oauth/handlers.ts
@@ -585,7 +585,10 @@ export function bearerMiddleware(
   }
   const token = trimmed.slice("Bearer".length).trim();
   if (!token) {
-    unauthorized(res, "invalid_token");
+    console.warn(
+      `[oauth] bearer_failure reason=empty_token ip=${oauthClientIp(req)}`,
+    );
+    unauthorizedWithDiscovery(req, res);
     return;
   }
 
@@ -610,11 +613,29 @@ export function bearerMiddleware(
       err instanceof InvalidAudience ||
       err instanceof MalformedToken
     ) {
-      unauthorized(res, "invalid_token");
+      // The catch block fans in four distinct JWT failure modes; tag the
+      // observability log with the actual reason so operators can tell
+      // signature drift apart from clock skew apart from aud mismatch
+      // (RFC 8707 resource binding) apart from a malformed token.
+      const reason =
+        err instanceof InvalidSignature
+          ? "invalid_signature"
+          : err instanceof TokenExpired
+            ? "expired"
+            : err instanceof InvalidAudience
+              ? "aud_mismatch"
+              : "malformed_token";
+      console.warn(
+        `[oauth] bearer_failure reason=${reason} ip=${oauthClientIp(req)}`,
+      );
+      unauthorizedWithDiscovery(req, res);
       return;
     }
     // Unknown error — fail closed
-    unauthorized(res, "invalid_token");
+    console.warn(
+      `[oauth] bearer_failure reason=unknown ip=${oauthClientIp(req)}`,
+    );
+    unauthorizedWithDiscovery(req, res);
   }
 }
 
@@ -628,7 +649,7 @@ function unauthorizedWithDiscovery(req: Request, res: Response): void {
   const resourceMetadata = `${origin}/.well-known/oauth-protected-resource`;
   res.setHeader(
     "WWW-Authenticate",
-    `Bearer realm="mcp", resource_metadata="${resourceMetadata}", scope="${TOKEN_SCOPE}"`,
+    `Bearer realm="mcp", resource_metadata="${resourceMetadata}", scope="${TOKEN_SCOPE}", error="invalid_token"`,
   );
   res.status(401).json({ error: "invalid_token" });
 }