diff --git a/src/config/environment.ts b/src/config/environment.ts
index 12059445..3abd6330 100644
--- a/src/config/environment.ts
+++ b/src/config/environment.ts
@@ -12,6 +12,11 @@ export interface AuthConfig {
   refreshSkewMs: number;
 }
 
+export interface JWTConfig {
+  /** Clock-skew tolerance in milliseconds for `exp`/`nbf` validation. */
+  clockSkewMs: number;
+}
+
 /**
  * Resolves the authentication token-lifecycle configuration, allowing the
  * refresh endpoint and skew to be overridden per environment via
@@ -27,3 +32,16 @@ export const getAuthConfig = (): AuthConfig => {
     refreshSkewMs: Number.isFinite(skew) && skew >= 0 ? skew : 60_000,
   };
 };
+
+/**
+ * Resolves JWT validation tolerance. Allows server-side clocks to differ slightly
+ * without rejecting otherwise valid tokens.
+ */
+export const getJWTConfig = (): JWTConfig => {
+  const skewRaw = process.env.JWT_CLOCK_SKEW_MS;
+  const skew = skewRaw ? Number.parseInt(skewRaw, 10) : NaN;
+
+  return {
+    clockSkewMs: Number.isFinite(skew) && skew >= 0 ? skew : 5_000,
+  };
+};
diff --git a/src/lib/auth/__tests__/jwt.test.ts b/src/lib/auth/__tests__/jwt.test.ts
new file mode 100644
index 00000000..c7a6c1f5
--- /dev/null
+++ b/src/lib/auth/__tests__/jwt.test.ts
@@ -0,0 +1,88 @@
+import { describe, expect, it, beforeEach, afterEach } from 'vitest';
+import { verifyToken, verifyTokenDetailed } from '../jwt';
+
+const SECRET = 'test-jwt-secret';
+const USER_ROLE = 'STUDENT' as const;
+
+function base64url(value: string): string {
+  return btoa(value).replace(/\+/g, '-').replace(/\//g, '_').replace(/=+$/g, '');
+}
+
+async function signTokenWithSecret(payload: Record<string, unknown>): Promise<string> {
+  const header = base64url(JSON.stringify({ alg: 'HS256', typ: 'JWT' }));
+  const body = base64url(JSON.stringify(payload));
+  const unsigned = `${header}.${body}`;
+  const key = await crypto.subtle.importKey(
+    'raw',
+    new TextEncoder().encode(SECRET),
+    { name: 'HMAC', hash: 'SHA-256' },
+    false,
+    ['sign'],
+  );
+  const signature = await crypto.subtle.sign('HMAC', key, new TextEncoder().encode(unsigned));
+  const signatureB64 = btoa(String.fromCharCode(...new Uint8Array(signature)))
+    .replace(/\+/g, '-')
+    .replace(/\//g, '_')
+    .replace(/=+$/g, '');
+  return `${unsigned}.${signatureB64}`;
+}
+
+describe('JWT clock skew tolerance', () => {
+  beforeEach(() => {
+    process.env.JWT_SECRET = SECRET;
+    process.env.JWT_CLOCK_SKEW_MS = '5000';
+  });
+
+  afterEach(() => {
+    delete process.env.JWT_SECRET;
+    delete process.env.JWT_CLOCK_SKEW_MS;
+  });
+
+  it('accepts exp and nbf timestamps within the configured leeway', async () => {
+    const nowSeconds = Math.floor(Date.now() / 1000);
+
+    const expiredSoon = await signTokenWithSecret({
+      sub: 'user-1',
+      role: USER_ROLE,
+      iat: nowSeconds - 10,
+      exp: nowSeconds - 2,
+    });
+
+    const notYetValid = await signTokenWithSecret({
+      sub: 'user-2',
+      role: USER_ROLE,
+      iat: nowSeconds - 10,
+      nbf: nowSeconds + 2,
+    });
+
+    await expect(verifyToken(expiredSoon)).resolves.not.toBeNull();
+    await expect(verifyToken(notYetValid)).resolves.not.toBeNull();
+
+    await expect(verifyTokenDetailed(expiredSoon)).resolves.toMatchObject({ valid: true });
+    await expect(verifyTokenDetailed(notYetValid)).resolves.toMatchObject({ valid: true });
+  });
+
+  it('rejects tokens beyond the allowed skew window', async () => {
+    const nowSeconds = Math.floor(Date.now() / 1000);
+
+    const expiredFarPast = await signTokenWithSecret({
+      sub: 'user-3',
+      role: USER_ROLE,
+      iat: nowSeconds - 60,
+      exp: nowSeconds - 10,
+    });
+
+    const notYetValidFarFuture = await signTokenWithSecret({
+      sub: 'user-4',
+      role: USER_ROLE,
+      iat: nowSeconds - 60,
+      nbf: nowSeconds + 10,
+    });
+
+    await expect(verifyToken(expiredFarPast)).resolves.toBeNull();
+    await expect(verifyToken(notYetValidFarFuture)).resolves.toBeNull();
+
+    await expect(verifyTokenDetailed(expiredFarPast)).resolves.toMatchObject({ valid: false, reason: 'expired' });
+    await expect(verifyTokenDetailed(notYetValidFarFuture)).resolves.toMatchObject({ valid: false, reason: 'not_yet_valid' });
+  });
+});
diff --git a/src/lib/auth/jwt.ts b/src/lib/auth/jwt.ts
index 705d3919..e3fa5ec6 100644
--- a/src/lib/auth/jwt.ts
+++ b/src/lib/auth/jwt.ts
@@ -1,4 +1,5 @@
 import { SignJWT } from 'jose';
+import { getJWTConfig } from '@/config/environment';
 import { UserRole } from '@/types/api';
 
 export interface JWTPayload {
@@ -32,6 +33,8 @@ const getSecret = () => {
   return new TextEncoder().encode(secret);
 };
 
+const getClockSkewSeconds = (): number => getJWTConfig().clockSkewMs / 1000;
+
 /**
  * Signs a new JWT for the given payload. Uses the `jose` library (Node runtime).
  */
@@ -85,7 +88,10 @@ export async function verifyToken(token: string | undefined | null): Promise<JWT
     const payloadJson = new TextDecoder().decode(base64UrlDecode(payloadB64));
     const payload = JSON.parse(payloadJson) as JWTPayload;
 
-    if (payload.exp && Date.now() / 1000 > payload.exp) return null;
+    const nowSeconds = Date.now() / 1000;
+    const clockSkewSeconds = getClockSkewSeconds();
+    if (payload.exp && nowSeconds > payload.exp + clockSkewSeconds) return null;
+    if (payload.nbf && nowSeconds < payload.nbf - clockSkewSeconds) return null;
 
     const validRoles: UserRole[] = [
       UserRole.ADMIN,
@@ -160,10 +166,11 @@ export async function verifyTokenDetailed(
     const payload = JSON.parse(new TextDecoder().decode(base64UrlDecode(payloadB64))) as JWTPayload;
 
     const nowSeconds = Date.now() / 1000;
-    if (payload.exp && nowSeconds > payload.exp) {
+    const clockSkewSeconds = getClockSkewSeconds();
+    if (payload.exp && nowSeconds > payload.exp + clockSkewSeconds) {
       return { valid: false, payload, reason: 'expired' };
     }
-    if (payload.nbf && nowSeconds < payload.nbf) {
+    if (payload.nbf && nowSeconds < payload.nbf - clockSkewSeconds) {
       return { valid: false, payload, reason: 'not_yet_valid' };
     }