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This article provides details about the various scenarios why your mailbox needs reauthorization. In such cases, you will see the "Please reauthorize your Email settings" banner on the Email Settings page. Based on the scenario, ensure that you complete the steps required for uninterrupted service.

This article contains:

Scenario 1: Microsoft Basic Authentication Depreciation and Migration to OAuth

Microsoft has deprecated Basic Authentication on online Exchange servers due to security protocols. OAuth, an open-standard authorization protocol, will replace Basic Authentication. OAuth secures designated access using authorization tokens, enhancing security without sharing password data.


If you use Microsoft as a custom mail server in Freshdesk and have already configured basic authentication, you will see a banner inside your helpdesk.


Follow the steps below to reauthorize your email.

  1. Navigate to Admin > Channels > Email.
  2. Click on Microsoft Office 365 and use Sign in with Microsoft to reauthorize your support mailbox.
  3. Enter your Microsoft credentials (username and password) to complete the reauthorization.
  4. The existing configuration will be replaced with OAuth-based configuration.
  5. Successful authentication will be confirmed with a message.

Note: This migration does not impact your helpdesk activities or email operations.


If you encounter errors in verifying the server name, port, and credentials: 

  1. Enable IMAP and Authenticated SMTP for authentication.

For New Microsoft OAuth Setup:

  1. Navigate to Admin > Channels > Email > New support email.
  2. Choose to use the mail server for Incoming only, Outgoing only, or Both.
  3. For Incoming only and Both, you can opt to delete emails from the server after fetching them to Freshdesk.
  4. Authenticate OAuth 2.0 using your Microsoft credentials. Successful authentication will be confirmed with a message.

Modifying Email Configuration:

  1. To switch to a new Microsoft account, enter the new account credentials and follow the normal procedure.
  2. To switch from a Gmail account to a Microsoft account, choose Microsoft Office 365, sign in with Microsoft, and follow the normal procedure.
Notes: 
1. View existing basic authentication details in the Others section. 
2. Provide the primary email address in the Your support email section if using a shared mailbox. 
3. OAuth is supported for personal accounts like Outlook.com and Hotmail.com.


You can refer to the using custom mail servers for incoming and outgoing emails to learn more.

Scenario 2: Reauthorization Required for Other and Gmail Mailbox

If you use the Gmail mailbox or the Other option and see a Reauthorization required message in Email settings, your password might have expired or changed. 

Check your username and provide your password again to reauthorize.

Scenario 3: Reauthorization Required for Microsoft Office 365 OAuth Mailbox

Microsoft credentials can expire for several reasons, such as password changes, caching conflicts, account closure, or inactivity. If you use Microsoft in Freshdesk, reauthorize your support mailbox.


Check if you've migrated to OAuth. If not, follow the steps in Scenario 1. If you still see a message, "Your Microsoft Office 365 credentials have expired. Please sign in again", do the following:

  1. Go to Admin > Channels > Email. 
  2. On the Email list page, click on the edit icon next to email configured with Microsoft Office 365. Sign in with Microsoft to complete the reauthorization.
  3. Click Save after each step to complete the authorization.

Scenario 4: Accounts with Multiple Support Emails

If the issue persists for accounts with multiple support emails, follow the steps below 

  • Navigate to Admin > Email.
  • Make the primary email non-primary.
  • Reauthorize the email.
  • Make the email primary again.

Note: Once you have completed the reauthorization, do the following:
  • Refresh your Freshdesk account or clear cache cookies from the browser. You can also check from an incognito window if the banner disappears.
  • If your agent email address is synced during the reauthorization process,  change the signed in account by clicking on the edit/ icon next to the email address.