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How to Fix MailMate Connection to Microsoft 365 Exchange Account
Question details
The user needs to connect the MailMate email client to an employer's Microsoft 365 Exchange account but is facing authentication failures because an app-specific password is required and the option is missing in security settings.
- Product
- MailMate and Microsoft 365 Exchange
- Device & OS
- Mac
- Scenario
- Setting up a corporate Microsoft 365 email account on the MailMate client for Mac.
- Observed behavior
- MailMate requests an app-specific password, but the account security settings do not show an option to create one. Enabling OAuth 2.0 either fails for sending mail or results in an unavailable-page error.
Verify that you have access to your Microsoft 365 security information page and check if your organization uses multi-factor authentication (MFA).
Configure MailMate for OAuth 2.0 Authentication
Use OAuth 2.0 instead of Basic Authentication, as Microsoft has deprecated basic auth for Exchange Online.
Exchange Online no longer supports basic authentication (standard username and password) for IMAP connections. Third-party clients like MailMate must use OAuth 2.0 to successfully authenticate with Microsoft 365 servers.
Launch MailMate on your Mac, go to 'Preferences', and select the 'Accounts' tab to edit your Microsoft 365 account.
Ensure the authentication method for both the Incoming (IMAP) and Outgoing (SMTP) server settings is set to OAuth 2.0.
Save the settings. MailMate should prompt you to open a web browser to log in with your employer credentials and grant MailMate permission to access your mailbox.
Contact Your Microsoft 365 Administrator
If app passwords are missing and OAuth 2.0 fails, you must request your IT administrator to adjust your account's security permissions.
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Frequently Asked Questions
Why is the app password option missing in my Microsoft 365 account?
Your organization's IT administrator has likely disabled the creation of app passwords for security reasons, usually to enforce modern authentication (OAuth 2.0) or strict multi-factor authentication (MFA) policies.
Why did MailMate suddenly stop connecting to Exchange Online?
Microsoft has permanently deprecated Basic Authentication for Exchange Online. Email clients that rely on simple username and password authentication will no longer connect unless they are updated and configured to use OAuth 2.0.
Can I still use IMAP with a Microsoft 365 employer account?
Yes, but you must use OAuth 2.0 for IMAP and SMTP connections. However, if your employer's Microsoft 365 tenant restricts third-party apps from using OAuth, IMAP connections will be blocked until the administrator grants permission.
