BoldDesk uses OAuth-based authentication for secure IMAP/SMTP access when connecting Microsoft email accounts. If an OAuth token expires or becomes invalid, inbound email synchronization and outbound email delivery may stop working until the connection is reauthenticated.

When reauthentication is required, BoldDesk displays an in-app notification to help administrators restore connectivity before email processing is affected.

Reauthenticate Microsoft OAuth (SMTP/IMAP)

1. Navigate to Admin → Emails.

2. Locate the affected support email address.

3. Click Edit next to the email.

4. Open the Server tab.

5. Click Reauthenticate for the Microsoft connection.
   

   
   
   

6. Complete the Microsoft sign-in process using the correct mailbox credentials.

7. Click Update to save the configuration.

Alternatively, you can click the “here” link in the banner notification, which will take you directly to the Support Emails page. From there, open the affected email using Edit and proceed with the reauthentication.

Reauthenticate IMAP for Gmail and Other Email Providers

If your support email is configured using Custom (IMAP) and authentication fails due to provider security requirements or blocked password sign-ins, generate an App Password and update it in the IMAP configuration.
Gmail commonly requires an App Password for IMAP connections when the regular account password is not accepted.

Steps to Reauthenticate IMAP for Gmail or Other Providers

1. Sign in to your email provider account and generate an App Password from the account’s Security settings.

   • For Gmail, App Passwords can be generated from Google Account → Security → App Passwords.
   • 2-Step Verification must be enabled before App Passwords become available.

2. In BoldDesk, navigate to Admin → Emails.

3. Open the support email configured with Custom (IMAP).

4. In the Incoming Emails (IMAP) section, replace the existing password with the generated App Password.

   • Verify the remaining IMAP settings, including:
     • Server
     • Port
     • SSL/TLS settings
     • Username

5. Click Update to save the configuration.
   

   
   
   

Once updated, BoldDesk will attempt to reconnect automatically and IMAP syncing will resume on the next sync cycle (it may take a few minutes).

Understanding Email Retrieval and Reauthentication in BoldDesk

When retrieving emails, BoldDesk currently supports fetching messages from the previous day only. This means emails older than 24 hours—such as those from two or three days ago—cannot be automatically retrieved. If a day is missed due to token expiration or another issue, those older emails will not be pulled into the system retroactively.

To prevent disruptions, it’s important to keep your Microsoft authentication token up to date. Microsoft provides a notification 10 days before a token expires, and BoldDesk will display an in-app banner as a reminder. Reauthentication is required every 90 days to maintain uninterrupted email fetching.

If emails were missed during the reauthentication period, they can still be recovered. Simply manually forward the missed emails—up to two weeks old—to your helpdesk email address. BoldDesk will process these messages and create corresponding tickets, ensuring no important communication is lost.

Troubleshooting

Reauthenticate Button Is Not Available

• Confirm that the support email is configured using Microsoft OAuth.
• Verify that your account has the necessary administrator permissions.
• Refresh the page and reopen the email configuration.
• Ensure you are viewing the Server tab.

Microsoft Login Keeps Selecting the Wrong Account

• Sign out of other Microsoft accounts in the browser.
• Open a private/incognito browser window.
• Sign in using the correct mailbox account.
• Restart the reauthentication process.

Emails Are Not Syncing After Reauthentication

• Verify that the reauthentication process completed successfully.
• Check whether new messages exist in the mailbox.
• Allow a few minutes for the next synchronization cycle.
• Review the email configuration for connection or authentication errors.
• Confirm that mailbox access has not been restricted by your email provider.

App Password Is Not Accepted

• Verify that the App Password was generated for the correct email account.
• Confirm that two-factor authentication is enabled where required.
• Check that the IMAP server settings match the provider’s recommended configuration.
• Generate a new App Password and try updating the configuration again.

Frequently Asked Questions

1. How often do Microsoft OAuth tokens require reauthentication for support email channels?
   Tokens follow Microsoft’s lifetime policy; BoldDesk guides admins to reauthenticate from Admin → Email when prompted by the in‑app banner.

2. We reconnected, but older emails didn’t import. Is that expected?
   Yes. After a gap, mail older than ~24 hours isn’t auto‑retrieved. Forward missed mail (up to two weeks) to your helpdesk address to ingest them as tickets.

3. During re‑auth, the browser selects the wrong Microsoft account. What should I do?
   Re‑authenticate in a private/incognito session or add the support mailbox as a separate browser account, then run Reauthenticate again.

4. Does BoldDesk support POP3 for syncing?
   No. BoldDesk supports IMAP for mailbox syncing (and forwarding as an alternative). POP3 is not available.

Related Articles

1. Configuring Support Email using IMAP with Microsoft OAuth in BoldDesk
2. How to Configure Support Email Addresses in BoldDesk