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PDF Upload Issues

File Size Too Large Error

Error Message: “File size too large. Please upload a file less than 10 MB.”
This error occurs when your PDF exceeds the 10 MB limit enforced in src/components/ui/FileUpload.tsx:38. Solutions:
  • Compress your PDF using online tools or PDF editing software
  • Split large documents into smaller PDFs
  • Remove high-resolution images or compress images within the PDF
  • Ensure your file is actually under 10 MB (check file properties)

Upload Fails Without Error

Symptoms: The upload appears to start but fails silently or gets stuck. Common Causes:
  1. Network timeout - Check your internet connection
  2. S3 configuration issues - Verify AWS credentials are set correctly
  3. File corruption - Try opening the PDF locally to ensure it’s not corrupted
  4. Browser issues - Clear cache and cookies, or try a different browser
Solutions:
1

Check file integrity

Open the PDF in a PDF reader to confirm it’s not corrupted
2

Refresh the page

Hard refresh your browser (Ctrl+Shift+R or Cmd+Shift+R)
3

Try again

Re-attempt the upload after a few minutes

Invalid File Format

Only PDF files with the .pdf extension are accepted. The upload component enforces this in src/components/ui/FileUpload.tsx:34.
Solutions:
  • Ensure your file has a .pdf extension
  • Convert other document formats (Word, Excel, etc.) to PDF first
  • Avoid renaming files from other formats to .pdf - use proper conversion

”Error uploading file” Toast Message

This generic error indicates an issue during the S3 upload process. Debugging Steps:
  1. Check browser console for detailed error messages (F12 → Console tab)
  2. Verify you’re logged in (authentication required)
  3. Ensure AWS S3 configuration is correct
  4. Try uploading a different, smaller PDF to isolate the issue

Chat Issues

”Error in creating chat” Message

This error occurs during chat creation after successful PDF upload (API endpoint: /api/create-chat).
Common Causes:
  • Pinecone vectorization failed
  • Database connection issues
  • Authentication token expired
  • S3 file key mismatch
Solutions:
  1. Re-upload the PDF - Start the process from scratch
  2. Check authentication - Log out and log back in
  3. Wait a moment - Server might be processing; try again in 30 seconds
  4. Contact support - If issue persists, provide your user ID and timestamp

AI Responses Are Slow or Timing Out

Possible Causes:
  • GPT-4 API rate limits
  • Large PDF with complex queries
  • Network latency
  • High server load
Solutions:
Complex questions about large documents may take 10-30 seconds to process. This is normal.
  • Be patient with initial responses (GPT-4 uses streaming)
  • Simplify your questions for faster responses
  • Avoid asking multiple questions simultaneously
  • Check your internet connection speed

AI Says “I don’t know” for Questions You Know Are in the PDF

Why This Happens: The AI retrieves context using semantic search. Sometimes:
  • The phrasing doesn’t match the document’s language
  • Information is in images or tables (not extracted as text)
  • The PDF has poor OCR quality
  • Context window doesn’t capture the relevant section
Solutions:
  • Rephrase your question using terms from the document
  • Ask more specific questions with context
  • Ensure your PDF contains selectable text (not just scanned images)
  • Break complex questions into smaller parts

Chat History Not Loading

Symptoms: Previous messages don’t appear or chat seems empty. Solutions:
  1. Refresh the page - Messages load from database on page load
  2. Check you’re viewing the correct chat - Use sidebar to navigate
  3. Verify authentication - Session might have expired
  4. Clear browser cache if issue persists

Subscription & Billing Issues

”Get Pro” Button Not Working

Symptoms: Clicking the button does nothing or shows an error. Common Causes:
  • Network issues preventing Stripe session creation
  • Authentication problems
  • Stripe configuration issues
Solutions:
1

Check browser console

Press F12 and look for error messages in the Console tab
2

Verify login status

Ensure you’re logged in and session is active
3

Try different browser

Test in incognito mode or another browser
4

Contact support

If issue persists, provide error details to support team

Payment Fails During Checkout

Payment processing is handled securely by Stripe. PDF AI uses INR currency with monthly billing.
Common Issues:
  • Card declined by bank
  • Insufficient funds
  • Card doesn’t support international transactions
  • 3D Secure authentication failed
Solutions:
  • Verify card details are entered correctly
  • Ensure your card supports online payments
  • Contact your bank to authorize the transaction
  • Try a different payment method
  • Check if your card supports INR transactions

Subscription Status Not Updating After Payment

Why This Happens: Webhook delays between Stripe and the application can cause temporary sync issues. Timeline:
  • Normal processing: Instant to 2 minutes
  • Webhook retry: Up to 30 minutes
Solutions:
  1. Wait 5 minutes - Refresh the page and check again
  2. Check email - Stripe sends confirmation emails
  3. Verify payment - Check your bank/card statement
  4. Log out and back in - Forces session refresh
  5. Contact support - If not resolved after 1 hour

Can’t Access Billing Portal

Symptoms: “Manage Subscriptions” button doesn’t work or shows error. Requirements:
  • You must have an active subscription
  • Must be logged in with the same account used for payment
  • Stripe customer ID must exist in database
Solutions:
  • Verify you have an active subscription
  • Check you’re logged in to the correct account
  • Clear cookies and re-authenticate
  • Contact support if you recently subscribed

Subscription Cancelled But Still Charged

Subscription cancellations take effect at the end of the current billing period. You retain access until then.
What to Know:
  • Cancellation is immediate, but access continues until period end
  • You won’t be charged for the next billing cycle
  • Partial refunds are not automatic
If incorrectly charged:
  1. Check the cancellation date in billing portal
  2. Verify the charge date matches your billing cycle
  3. Contact support with transaction details for refund requests

Authentication Issues

”Unauthorized” Error (401)

This occurs when API requests are made without valid authentication. Common Scenarios:
  • Session expired
  • Not logged in
  • Cookie issues
  • Clerk authentication failed
Solutions:
  • Log out completely and log back in
  • Clear browser cookies for the site
  • Check if third-party cookies are enabled
  • Try in incognito mode to rule out extensions

Logged Out Unexpectedly

Causes:
  • Session timeout
  • Browser cleared cookies
  • Multiple tabs/windows causing conflicts
Prevention:
  • Stay active on the platform
  • Avoid clearing cookies while using the app
  • Use a single tab/window for the application

Database & Data Issues

Chat Missing from Sidebar

Possible Reasons:
  • Chat was created under a different account
  • Database sync delay
  • Chat creation actually failed (check for error toast)
Solutions:
  1. Refresh the page to reload chat list
  2. Verify you’re logged in to the correct account
  3. Check if the PDF upload completed successfully
  4. Re-upload if necessary

PDF Viewer Not Displaying

Common Causes:
  • S3 URL access issues
  • CORS configuration problems
  • PDF file corruption
  • Browser PDF rendering issues
Solutions:
  • Try a different browser
  • Check browser console for CORS errors
  • Ensure browser can display PDFs natively
  • Re-upload the PDF if consistently failing

General Troubleshooting Steps

When experiencing any issue:
1

Check browser console

Press F12 → Console tab to see detailed error messages
2

Verify authentication

Ensure you’re logged in and session is active
3

Clear cache

Hard refresh (Ctrl+Shift+R) or clear browser cache
4

Try different browser

Test in Chrome, Firefox, or Safari to isolate browser-specific issues
5

Check internet connection

Ensure stable connection for uploads and chat streaming
6

Wait and retry

Some issues resolve with temporary server issues; wait 5-10 minutes
If you’ve tried all relevant troubleshooting steps and the issue persists, contact support with:
  • Description of the issue
  • Browser and version
  • Screenshots of errors
  • Your user ID or email
  • Timestamp when issue occurred

Error Code Reference

Error CodeMeaningLocation
401Unauthorized - authentication requiredMultiple API routes
404Chat not found/api/chat
500Internal server errorMultiple API routes

Still Need Help?

If your issue isn’t covered here:
  • Check the FAQ for additional information
  • Review the API documentation for technical details
  • Contact support with detailed information about your issue

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