diff --git a/src/browser/client.ts b/src/browser/client.ts
index 368a845..a7c5cc1 100644
--- a/src/browser/client.ts
+++ b/src/browser/client.ts
@@ -6,6 +6,7 @@ import fs from 'fs';
 
 export class BrowserClient {
   private context: BrowserContext | null = null;
+  private sessionDir: string | null = null;
 
   constructor(
     private config: Config,
@@ -14,6 +15,7 @@ export class BrowserClient {
 
   async initialize(): Promise<BrowserContext> {
     const sessionDir = path.resolve(process.cwd(), this.config.browser.sessionDir);
+    this.sessionDir = sessionDir;
 
     // Ensure session directory exists
     if (!fs.existsSync(sessionDir)) {
@@ -171,6 +173,26 @@ export class BrowserClient {
         page.waitForURL((url) => !url.toString().includes('/login'), { timeout: 20000 }).catch(() => undefined),
       ]);
 
+      // Give cookies/time to settle
+      await page.waitForTimeout(2000);
+
+      const obstacleInfo = await this.detectLoginObstacles(page);
+      if (obstacleInfo.twoFactor) {
+        this.logger.error('Login requires 2FA. Please run "npm run login" locally to complete it once.');
+        await this.captureLoginDebug(page, 'login-2fa');
+        return false;
+      }
+      if (obstacleInfo.captcha) {
+        this.logger.error('Login blocked by CAPTCHA. Please run "npm run login" locally to complete it once.');
+        await this.captureLoginDebug(page, 'login-captcha');
+        return false;
+      }
+      if (obstacleInfo.errorText) {
+        this.logger.error(`Login failed with error: ${obstacleInfo.errorText}`);
+        await this.captureLoginDebug(page, 'login-error');
+        return false;
+      }
+
       // Confirm auth via UI or API check
       const isValid = await this.isSessionValid();
       if (isValid) {
@@ -179,10 +201,7 @@ export class BrowserClient {
       }
 
       // Check for error messages
-      const errorContent = await page.evaluate(() => {
-        const err = document.querySelector('[role="alert"], .AnimatedForm__errorMessage');
-        return err ? err.textContent : null;
-      });
+      const errorContent = obstacleInfo.errorText;
 
       if (errorContent) {
         this.logger.error(`Login failed with error: ${errorContent}`);
@@ -190,6 +209,7 @@ export class BrowserClient {
         this.logger.error('Login flow finished but session is invalid.');
       }
 
+      await this.captureLoginDebug(page, 'login-invalid-session');
       return false;
 
     } catch (error) {
@@ -197,4 +217,67 @@ export class BrowserClient {
       return false;
     }
   }
+
+  private async detectLoginObstacles(page: Page): Promise<{
+    twoFactor: boolean;
+    captcha: boolean;
+    errorText: string | null;
+  }> {
+    try {
+      const info = await page.evaluate(() => {
+        const errorCandidates = Array.from(
+          document.querySelectorAll('[role="alert"], .AnimatedForm__errorMessage, [data-testid*="error"], [id*="error"]')
+        )
+          .map((el) => el.textContent?.trim())
+          .filter((text) => text && text.length > 0) as string[];
+
+        const otpInput = document.querySelector('input[name="otp"], input[autocomplete="one-time-code"], input[type="tel"][maxlength="6"]');
+        const captchaElement = document.querySelector('iframe[src*="captcha"], iframe[src*="recaptcha"], [data-sitekey], #captcha, .captcha');
+
+        return {
+          errorText: errorCandidates[0] ?? null,
+          hasOtp: Boolean(otpInput),
+          hasCaptcha: Boolean(captchaElement),
+        };
+      });
+
+      const frameCaptcha = page.frames().some((frame) => /captcha|recaptcha/i.test(frame.url()));
+
+      return {
+        twoFactor: info.hasOtp,
+        captcha: info.hasCaptcha || frameCaptcha,
+        errorText: info.errorText,
+      };
+    } catch {
+      return { twoFactor: false, captcha: false, errorText: null };
+    }
+  }
+
+  private async captureLoginDebug(page: Page, label: string): Promise<void> {
+    try {
+      const baseDir = this.sessionDir ?? path.resolve(process.cwd(), 'data');
+      if (!fs.existsSync(baseDir)) {
+        fs.mkdirSync(baseDir, { recursive: true });
+      }
+
+      const safeTimestamp = new Date().toISOString().replace(/[:.]/g, '-');
+      const screenshotPath = path.join(baseDir, `${label}-${safeTimestamp}.png`);
+      const htmlPath = path.join(baseDir, `${label}-${safeTimestamp}.html`);
+
+      await page.screenshot({ path: screenshotPath, fullPage: true }).catch(() => undefined);
+      const html = await page.content().catch(() => '');
+      if (html) {
+        fs.writeFileSync(htmlPath, html, 'utf-8');
+      }
+
+      this.logger.info(`Saved login debug artifacts to ${screenshotPath} and ${htmlPath}`);
+      this.logger.info(`Login debug URL: ${page.url()}`);
+      const title = await page.title().catch(() => '');
+      if (title) {
+        this.logger.info(`Login debug title: ${title}`);
+      }
+    } catch (error) {
+      this.logger.warn('Failed to capture login debug artifacts:', error);
+    }
+  }
 }