Microsoft OAuth tokens used for SMTP/IMAP authentication expire every 90 days. If a Microsoft-based support email configured in BoldDesk has an OAuth token that is expired or nearing expiration, the support email must be reauthenticated to maintain uninterrupted email synchronization and sending. If the Microsoft OAuth token expires and is not reauthenticated, BoldDesk will be unable to retrieve new emails from the mailbox or send outgoing emails through the connected support email. This may result in delayed ticket creation, failed email replies, and interrupted customer communication.

When Reauthentication is Required

Reauthenticate the Microsoft-connected support email in BoldDesk when any of the following occurs:

• Incoming email synchronization stops for a Microsoft mailbox connected using OAuth (IMAP).
• Outgoing email sending fails for a Microsoft mailbox connected using OAuth (SMTP).
• The OAuth token is nearing expiration or has already expired (Microsoft token lifetime is 90 days).

Reauthenticating a Microsoft-connected Support Email (OAuth)

Follow the steps below to reauthenticate a Microsoft-connected support email.

1. Navigate to Admin > Emails.
2. Click on the edit icon on the required support email.
3. Confirm the option connect a support email address is checked and click next.
4. On this page, locate and click the Reauthenticate button under incoming emails.
   
   
   
   
   
5. You will be redirected to the Microsoft Login page. Complete the login process to reauthenticate your email.

Following these steps will help maintain seamless email operations and ensure continued access to your Microsoft email services.

Troubleshooting

Microsoft login page does not complete authentication

• Confirm the Microsoft credentials match the same mailbox configured in BoldDesk.
• Restart the flow from Admin → Emails → Edit → Next → Reauthenticate.

Email operations do not resume after reauthentication

• Wait a few minutes for the next synchronization cycle, then retest:
  • incoming email → ticket creation behavior
  • outgoing email → sending behavior

Reauthenticate button is not visible

• Verify the support email was configured using Microsoft OAuth.
• Password-based IMAP configurations do not display the Reauthenticate option.

Microsoft shows consent or permission errors

• Ensure required Microsoft permissions have not been revoked by your Microsoft 365 administrator.
• Complete the authentication using an account with access to the configured mailbox.

Frequently Asked Questions

1. Why do Microsoft OAuth tokens expire every 90 days?
   Microsoft enforces token expiration as a security control. BoldDesk must reauthenticate to continue using OAuth for IMAP/SMTP access.

2. When should the Microsoft mailbox be reauthenticated?
   Reauthenticate when the token is near expiration, already expired, or when IMAP/SMTP operations fail due to OAuth authentication issues.

3. Where is the Reauthenticate button in BoldDesk?
   Admin → Emails → Support Emails → Edit (pencil) → Next → Incoming Emails → Reauthenticate

4. Does reauthentication require admin access?
   Yes. The process requires admin-level access to Admin → Emails and edit permissions for support email settings.

5. What happens after clicking Reauthenticate?
   BoldDesk redirects to the Microsoft login page. After sign-in completes, the OAuth authorization is refreshed for the configured support email.

6. Do non-Microsoft mail providers require this same reauthentication process?
   This procedure applies to Microsoft OAuth connections. Other providers may use passwords, app passwords, or provider-specific OAuth processes.

7. Is reauthentication needed if only outgoing sending fails?
   Yes. SMTP sending failures for a Microsoft OAuth mailbox can indicate the OAuth authorization needs to be refreshed.

8. Is reauthentication needed if only incoming synchronization stops?
   Yes. IMAP synchronization failures for a Microsoft OAuth mailbox can indicate the OAuth authorization needs to be refreshed.

9. How can I identify that a support email requires reauthentication?
   BoldDesk displays authentication-related errors in the BoldDesk agent portal banner when OAuth token is invalid, expired, or cannot be refreshed. Review the email connection status under Admin → Emails.

10. Does reauthentication update both IMAP and SMTP authentication?
    Yes. Reauthenticating the Microsoft OAuth connection refreshes the authorization used for both incoming email synchronization (IMAP) and outgoing email sending (SMTP). Outgoing emails use the same configuration as incoming emails.

Related Articles

1. How to Configure Support Email using IMAP with Microsoft OAuth in BoldDesk
2. How to Configure IMAP in BoldDesk for Email Synchronization