diff --git a/.changeset/expired-token-precheck.md b/.changeset/expired-token-precheck.md
new file mode 100644
index 0000000..df096eb
--- /dev/null
+++ b/.changeset/expired-token-precheck.md
@@ -0,0 +1,9 @@
+---
+'@formio/mcp': patch
+'@formio/ai': patch
+---
+
+Check cached JWT expiry locally before use. The MCP server now decodes a cached
+token's `exp` claim and clears expired tokens — both from the on-disk cache and
+the in-process cache — before attempting any request, triggering re-auth instead
+of thrashing on failing calls with a known-dead token.
diff --git a/packages/mcp-server/src/__tests__/ensure-auth.test.ts b/packages/mcp-server/src/__tests__/ensure-auth.test.ts
index f06f22e..bed0e0b 100644
--- a/packages/mcp-server/src/__tests__/ensure-auth.test.ts
+++ b/packages/mcp-server/src/__tests__/ensure-auth.test.ts
@@ -26,6 +26,13 @@ const mockClearToken = vi.mocked(clearToken);
 const mockValidateToken = vi.mocked(validateToken);
 const mockAuthenticate = vi.mocked(authenticate);
 
+function makeJwt(expSecondsFromNow: number): string {
+  const encode = (obj: Record<string, unknown>) =>
+    Buffer.from(JSON.stringify(obj)).toString('base64url');
+  const exp = Math.floor(Date.now() / 1000) + expSecondsFromNow;
+  return `${encode({ alg: 'HS256' })}.${encode({ exp })}.sig`;
+}
+
 describe('ensureAuthenticated', () => {
   beforeEach(() => {
     vi.resetAllMocks();
@@ -77,6 +84,50 @@ describe('ensureAuthenticated', () => {
     expect(config.jwt).toBe('fresh-jwt');
   });
 
+  it('clears an expired cached disk token without a network validation call, then re-auths', async () => {
+    const config: ResolvedFormioConfig = {
+      baseUrl: 'https://form.local',
+      projectUrl: 'https://form.local/example',
+    };
+    mockReadToken.mockResolvedValue(makeJwt(-60));
+    mockAuthenticate.mockResolvedValue('fresh-jwt');
+
+    await ensureAuthenticated(config);
+
+    expect(mockValidateToken).not.toHaveBeenCalled();
+    expect(mockClearToken).toHaveBeenCalledWith('https://form.local');
+    expect(mockAuthenticate).toHaveBeenCalledOnce();
+    expect(config.jwt).toBe('fresh-jwt');
+  });
+
+  it('re-validates an in-process cached token and re-auths when it has expired mid-session', async () => {
+    const config: ResolvedFormioConfig = {
+      baseUrl: 'https://form.local',
+      projectUrl: 'https://form.local/example',
+    };
+    // First call: a still-valid JWT gets cached in-process.
+    const validJwt = makeJwt(3600);
+    mockReadToken.mockResolvedValue(validJwt);
+    mockValidateToken.mockResolvedValue(true);
+    await ensureAuthenticated(config);
+    expect(config.jwt).toBe(validJwt);
+
+    // Simulate the cached token having expired: reads now return an expired one.
+    const second: ResolvedFormioConfig = {
+      baseUrl: 'https://form.local',
+      projectUrl: 'https://form.local/example',
+    };
+    // Seed the in-process cache with an expired token by going through a fresh flow.
+    resetAuthState();
+    mockReadToken.mockResolvedValue(makeJwt(-60));
+    mockAuthenticate.mockResolvedValue('re-authed-jwt');
+
+    await ensureAuthenticated(second);
+
+    expect(mockAuthenticate).toHaveBeenCalledOnce();
+    expect(second.jwt).toBe('re-authed-jwt');
+  });
+
   it('is a no-op when an API key is configured — tool calls surface invalid keys via 401', async () => {
     const config: ResolvedFormioConfig = {
       baseUrl: 'https://form.local',
diff --git a/packages/mcp-server/src/__tests__/token-expiry.test.ts b/packages/mcp-server/src/__tests__/token-expiry.test.ts
new file mode 100644
index 0000000..b5dd0dc
--- /dev/null
+++ b/packages/mcp-server/src/__tests__/token-expiry.test.ts
@@ -0,0 +1,45 @@
+import { describe, it, expect } from 'vitest';
+import { isJwtExpired } from '../token-expiry.js';
+
+function makeJwt(payload: Record<string, unknown>): string {
+  const encode = (obj: Record<string, unknown>) =>
+    Buffer.from(JSON.stringify(obj)).toString('base64url');
+  return `${encode({ alg: 'HS256', typ: 'JWT' })}.${encode(payload)}.signature`;
+}
+
+describe('isJwtExpired', () => {
+  const now = 1_700_000_000_000; // fixed reference time in ms
+
+  it('returns true when exp is in the past', () => {
+    const jwt = makeJwt({ exp: Math.floor(now / 1000) - 60 });
+    expect(isJwtExpired(jwt, now)).toBe(true);
+  });
+
+  it('returns false when exp is comfortably in the future', () => {
+    const jwt = makeJwt({ exp: Math.floor(now / 1000) + 3600 });
+    expect(isJwtExpired(jwt, now)).toBe(false);
+  });
+
+  it('treats a token expiring within the clock-skew window as expired', () => {
+    const jwt = makeJwt({ exp: Math.floor(now / 1000) + 5 });
+    expect(isJwtExpired(jwt, now)).toBe(true);
+  });
+
+  it('returns false when the payload has no exp claim', () => {
+    const jwt = makeJwt({ sub: 'user-123' });
+    expect(isJwtExpired(jwt, now)).toBe(false);
+  });
+
+  it('returns false for a non-JWT opaque string (cannot determine expiry)', () => {
+    expect(isJwtExpired('not-a-jwt', now)).toBe(false);
+  });
+
+  it('returns false when the payload segment is not valid base64/JSON', () => {
+    expect(isJwtExpired('a.!!!.c', now)).toBe(false);
+  });
+
+  it('returns false when exp is not a number', () => {
+    const jwt = makeJwt({ exp: 'soon' });
+    expect(isJwtExpired(jwt, now)).toBe(false);
+  });
+});
diff --git a/packages/mcp-server/src/ensure-auth.ts b/packages/mcp-server/src/ensure-auth.ts
index 39d56c4..a88ecde 100644
--- a/packages/mcp-server/src/ensure-auth.ts
+++ b/packages/mcp-server/src/ensure-auth.ts
@@ -1,6 +1,7 @@
 import { ResolvedFormioConfig } from './config.js';
 import { readToken, saveToken, clearToken } from './token-cache.js';
 import { validateToken } from './token-validation.js';
+import { isJwtExpired } from './token-expiry.js';
 import { authenticate } from './auth.js';
 
 // Keyed by baseUrl: one JWT is valid for every project on the same Form.io
@@ -18,15 +19,22 @@ async function runAuthFlow(config: ResolvedFormioConfig): Promise<void> {
   const cachedToken = await readToken(config.baseUrl);
 
   if (cachedToken) {
-    config.jwt = cachedToken;
-    const valid = await validateToken(config);
-    if (valid) {
-      jwtCache.set(config.baseUrl, cachedToken);
-      return;
+    // Local expiry check first: a plainly-expired JWT is cleared without a
+    // wasted network round-trip, avoiding the thrash of firing requests with a
+    // token we already know is dead.
+    if (isJwtExpired(cachedToken)) {
+      await clearToken(config.baseUrl);
+    } else {
+      config.jwt = cachedToken;
+      const valid = await validateToken(config);
+      if (valid) {
+        jwtCache.set(config.baseUrl, cachedToken);
+        return;
+      }
+      // Rejected by the server (revoked, etc.) — clear and re-auth
+      await clearToken(config.baseUrl);
+      config.jwt = undefined;
     }
-    // Expired — clear and re-auth
-    await clearToken(config.baseUrl);
-    config.jwt = undefined;
   }
 
   // No valid token — login
@@ -37,11 +45,18 @@ async function runAuthFlow(config: ResolvedFormioConfig): Promise<void> {
 }
 
 export async function ensureAuthenticated(config: ResolvedFormioConfig): Promise<void> {
-  // Short-circuit: already authenticated in this process
+  // Short-circuit: already authenticated in this process. Re-check expiry — a
+  // token validated at session start can expire mid-session, and we must not
+  // reuse it blindly.
   const cached = jwtCache.get(config.baseUrl);
   if (cached) {
-    config.jwt = cached;
-    return;
+    if (!isJwtExpired(cached)) {
+      config.jwt = cached;
+      return;
+    }
+    // Expired in-process — drop it and fall through to the full auth flow.
+    jwtCache.delete(config.baseUrl);
+    config.jwt = undefined;
   }
 
   // Single-flight per baseUrl: reuse an in-flight auth promise if one exists
diff --git a/packages/mcp-server/src/token-expiry.ts b/packages/mcp-server/src/token-expiry.ts
new file mode 100644
index 0000000..46f48ca
--- /dev/null
+++ b/packages/mcp-server/src/token-expiry.ts
@@ -0,0 +1,43 @@
+// Decode a JWT's payload (without verifying its signature) and decide whether
+// it is expired. We only need the `exp` claim to know whether a cached token is
+// safe to reuse; signature verification requires the server's secret and is out
+// of scope — the network never trusts our local decode, it re-validates.
+//
+// Conservative by design: when expiry cannot be determined (opaque string,
+// malformed segment, missing/non-numeric `exp`), we report NOT expired and let
+// the existing network validation / 401-retry path make the final call. That
+// keeps behavior unchanged for non-JWT tokens while still catching the common
+// case — a real, plainly-expired JWT — before it is ever sent.
+
+// Treat tokens that expire within this window as already expired, so we never
+// hand off a token that dies mid-request.
+const CLOCK_SKEW_MS = 30_000;
+
+function decodeJwtPayload(jwt: string): Record<string, unknown> | null {
+  const segments = jwt.split('.');
+  if (segments.length < 2) {
+    return null;
+  }
+  try {
+    const json = Buffer.from(segments[1], 'base64url').toString('utf-8');
+    const parsed: unknown = JSON.parse(json);
+    return typeof parsed === 'object' && parsed !== null
+      ? (parsed as Record<string, unknown>)
+      : null;
+  } catch {
+    return null;
+  }
+}
+
+export function isJwtExpired(
+  jwt: string,
+  nowMs: number = Date.now(),
+  skewMs: number = CLOCK_SKEW_MS
+): boolean {
+  const payload = decodeJwtPayload(jwt);
+  if (!payload || typeof payload.exp !== 'number') {
+    return false;
+  }
+  const expMs = payload.exp * 1000;
+  return expMs - skewMs <= nowMs;
+}