Microsoft 365 Issues

Common problems with Microsoft 365 SSO login and Outlook email integration.

SSO Login Issues

"Sign in with Microsoft" Does Nothing

1. Check that Supabase Dashboard → Authentication → Providers → Azure is enabled
2. Verify the Azure Client ID and Secret are correct
3. Ensure the redirect URI https://<project-ref>.supabase.co/auth/v1/callback is registered in Azure AD

"AADSTS50011: The redirect URI does not match"

Add this exact URL to Azure AD → Authentication → Web redirect URIs:

https://<project-ref>.supabase.co/auth/v1/callback

User Created but No Workspace

• Check /auth/callback handling — workspace creation may have failed
• Look at Supabase Edge Function logs for errors during onboarding
• Manually create a workspace via Settings → Workspace

Email Connection Issues

"OAuth session expired" on Callback

• The httpOnly cookie wasn't sent by the browser
• Check that your domain supports cookies (not localhost without HTTPS)
• Ensure SameSite=Lax and Secure flags are set correctly

"Failed to obtain access token"

• Client secret may be wrong or expired
• Go to Azure Portal → Certificates & secrets and verify
• Regenerate the secret if needed and update MICROSOFT_CLIENT_SECRET

"AADSTS700016: Application not found"

• Wrong MICROSOFT_CLIENT_ID
• Or the app registration was deleted
• Verify the Client ID matches your Azure AD app

Sync Issues

Emails Not Syncing

1. Check user_email_connections.is_active — may be deactivated after 10 errors
2. Check user_email_connections.connection_error for details
3. Verify NEXT_PUBLIC_APP_URL is set correctly (not localhost on production)

Token Refresh Fails

• Refresh token may be revoked by user or admin
• MICROSOFT_CLIENT_SECRET may have expired
• User needs to reconnect their account

Webhook Issues

Webhooks Not Receiving Notifications

1. Verify https://workspace.leenops.com/api/webhooks/outlook is publicly accessible
2. Check subscription hasn't expired (3-day max TTL for Microsoft)
3. Verify user_email_connections.webhook_subscription_id is set
4. Check MICROSOFT_WEBHOOK_SECRET environment variable is configured

Admin Consent Issues

"AADSTS90094: Admin consent is required"

Your organization requires admin approval. Options:

1. Ask your IT admin to approve Leenops in Azure AD
2. If you're an admin, use the Admin Consent flow:
   • Navigate to /api/auth/outlook/admin-consent
   • Sign in as an Azure AD Global Admin or Application Admin
   • Approve for the entire organization

Environment Variables Checklist