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1.6. Troubleshooting O365 OAuth Mailboxes

This document provides troubleshooting guidance for HelpSpot Email Mailboxes connected to O365 email accounts. If you're experiencing trouble with mailflow or if you received an email error notification in HelpSpot, the tips below can help you identify and correct many common problems. 

Connectivity

To begin with, the Admin > Email Mailboxes page displays each mailbox's Last Successful Check timestamp. If this reflects the current time, it means connectivity to the email account is working. If the Last Successful Check reflects any timestamp more than 1-2 minutes old, it means that was the last time that HelpSpot was able to successfully connect to the email account. Stale Last Check times sometimes offer clues to the cause of such issues (new firewall rules applied at a known time, network changes affecting on-prem HelpSpot servers, etc.)

If you see stale Last Check times, the first recommendation for restoring connectivity is to regenerate the API token  from https://auth.helpspot.com. Make sure you use an incognito/private browsing window to prevent any account caching issues. Generate the token in an incognito window and paste it into your mailbox settings in HelpSpot to attempt reconnecting to the email account.

If the Last Check is already current or if it still isn't refreshing after generating a new API key, the next most-likely cause is that the HelpSpot services aren't running correctly.

Queue Worker Services

• Troubleshooting HelpSpot Cloud Queue Worker Services
• Troubleshooting On-Premise Queue Worker Services

Other Issues

Lastly, if the services are running and you're still not getting incoming mail, you can temporarily bump up your logging output to include the details of each mail check action. Follow these directions to enable debug logging.

Contact Support

If none of the above tips resolves your email issue, reach out to HelpSpot Support for further troubleshooting assistance. You can include your helpspot.log file (or email-related stack trace excerpts from it if it's very large) when you submit your request.