diff --git a/packages/sdk/src/client/client.ts b/packages/sdk/src/client/client.ts
index d32a51dd4..24a9afab4 100644
--- a/packages/sdk/src/client/client.ts
+++ b/packages/sdk/src/client/client.ts
@@ -882,6 +882,7 @@ export class Client {
     }
 
     this.conditions[ClientCondition.WatchLoop] = true;
+    let retryCount = 0;
     return attachment.runWatchLoop(
       (onDisconnect: () => void): Promise<[WatchStream, AbortController]> => {
         if (!this.isActive()) {
@@ -948,6 +949,15 @@ export class Client {
                   err instanceof ConnectError &&
                   errorCodeOf(err) === Code.ErrUnauthenticated
                 ) {
+                  if (retryCount >= this.maxRequestRetries) {
+                    logger.error(
+                      `[WD] c:"${this.getKey()}" max retries (${
+                        this.maxRequestRetries
+                      }) exceeded`,
+                    );
+                    reject(err);
+                    return;
+                  }
                   attachment.doc.publish([
                     {
                       type: DocEventType.AuthError,
@@ -959,6 +969,7 @@ export class Client {
                   ]);
                 }
                 onDisconnect();
+                retryCount++;
               } else {
                 this.conditions[ClientCondition.WatchLoop] = false;
               }
diff --git a/packages/sdk/test/integration/webhook_test.ts b/packages/sdk/test/integration/webhook_test.ts
index c493d5a0a..b49736852 100644
--- a/packages/sdk/test/integration/webhook_test.ts
+++ b/packages/sdk/test/integration/webhook_test.ts
@@ -19,6 +19,7 @@ import { describe, it, vi, beforeAll, afterAll, expect } from 'vitest';
 import yorkie, {
   SyncMode,
   DocumentSyncStatus,
+  DocEventType,
 } from '@yorkie-js-sdk/src/yorkie';
 import {
   assertThrowsAsync,
@@ -353,4 +354,100 @@ describe('Auth Webhook', () => {
     await client.detach(doc);
     await client.deactivate();
   });
+
+  it('should refresh token and retry watch document', async ({ task }) => {
+    // Create New project
+    const projectResponse = await axios.post(
+      `${testRPCAddr}/yorkie.v1.AdminService/CreateProject`,
+      { name: `auth-webhook-${new Date().getTime()}` },
+      {
+        headers: { Authorization: adminToken },
+      },
+    );
+    const projectId = projectResponse.data.project.id;
+    apiKey = projectResponse.data.project.publicKey;
+
+    // Update project with webhook url and methods
+    await axios.post(
+      `${testRPCAddr}/yorkie.v1.AdminService/UpdateProject`,
+      {
+        id: projectId,
+        fields: {
+          auth_webhook_url: `http://127.0.0.1:${webhookServerPort}/auth-webhook`,
+          auth_webhook_methods: { methods: ['WatchDocuments'] },
+        },
+      },
+      {
+        headers: { Authorization: adminToken },
+      },
+    );
+
+    const TokenExpirationMs = 2000;
+    const authTokenInjector = vi.fn(async (authErrorMessage) => {
+      if (authErrorMessage === ExpiredTokenErrorMessage) {
+        return `token-${Date.now() + TokenExpirationMs}`;
+      }
+      return `token-${Date.now()}`;
+    });
+    // client with token
+    const client = new yorkie.Client(testRPCAddr, {
+      apiKey,
+      authTokenInjector,
+      retryRequestDelay: 0,
+    });
+
+    await client.activate();
+    const docKey = toDocKey(`${task.name}-${new Date().getTime()}`);
+    const doc = new yorkie.Document<{ k1: string }>(docKey);
+
+    const authErrorEventCollector = new EventCollector<{
+      errorMessage: string;
+      method: string;
+    }>();
+    doc.subscribe('auth-error', (event) => {
+      authErrorEventCollector.add(event.value);
+    });
+
+    // Another client for verifying if the watchDocument is working properly
+    const client2 = new yorkie.Client(testRPCAddr, {
+      apiKey,
+      authTokenInjector: async () => {
+        return `token-${Date.now() + 1000 * 60 * 60}`; // expire in 1 hour
+      },
+      retryRequestDelay: 0,
+    });
+    await client2.activate();
+    const doc2 = new yorkie.Document<{ k1: string }>(docKey);
+    await client2.attach(doc2);
+
+    const presenceEventCollector = new EventCollector();
+    doc2.subscribe('presence', (event) => {
+      presenceEventCollector.add(event.type);
+    });
+
+    // retry watch document
+    await new Promise((res) => setTimeout(res, TokenExpirationMs));
+    await client.attach(doc);
+    await authErrorEventCollector.waitFor({
+      errorMessage: ExpiredTokenErrorMessage,
+      method: 'WatchDocuments',
+    });
+    expect(authTokenInjector).toBeCalledTimes(2);
+    expect(authTokenInjector).nthCalledWith(1);
+    expect(authTokenInjector).nthCalledWith(2, ExpiredTokenErrorMessage);
+    await presenceEventCollector.waitFor(DocEventType.Watched);
+
+    const syncEventCollector = new EventCollector();
+    doc.subscribe('sync', (event) => {
+      syncEventCollector.add(event.value);
+    });
+    doc2.update((root) => {
+      root.k1 = 'v1';
+    });
+    await syncEventCollector.waitFor(DocumentSyncStatus.Synced);
+    expect(doc.getRoot().k1).toBe('v1');
+
+    await client.detach(doc);
+    await client.deactivate();
+  });
 });