Cannot Authenticate to my Live.com Email Account via OAuth

Question

For a few years now, my external email clients have not been able to authenticate to my live account. I have a custom domain from many years ago when they allowed them for free. For a little while, I was able to use an alternate gmail email address to log in - which seemed weird but it worked. Now I can't get oauth to work at all and haven't been able to for probably a year or two. Now these emails are getting neglected and I can't even go in and sync / export because the only way I can access the account is via the web.

I get the impression it has something to do with my account being associated with a work account and a personal account - even though I have no paid work accounts - I think it's trying to associate with the wrong account and it can't log in. I don't get anything useful - I just get an error that "an error occurred authorizing".

Answer 1

Hello Todd Brown, 

Thank you for reaching out to Microsoft Q&A. I understand how frustrating it is to be locked out of your own email clients, especially when you have been successfully using this custom domain for so many years.  

Your intuition about the "Work vs. Personal" account conflict is exactly what is causing this "error occurred authorizing" message. 

To fix this, we need to give your email client a login name that the Microsoft servers will immediately recognize as a purely Personal account. We do this by creating a native @outlook.com alias. 

Step 1: Create the Alias 

• Log into your Microsoft account via a web browser at https://www.google.com/search?q=account.microsoft.com. 
• Go to Your info at the top, and then select Sign-in preferences (or "Manage how you sign in to Microsoft"). 
• Click Add email and choose to create a new email address ending in @outlook.com. 
• CRITICAL NOTE: Please do not remove or delete your legacy custom domain from this list! Simply add the new @outlook.com address alongside it. 

Step 2: Update Your Sign-in Preferences 

• On that same page, look at the bottom for Change sign-in preferences. 
• Make sure the box next to your newly created @outlook.com alias is checked, allowing it to be used to log in. 

Step 3: Reconnect Your Email Client 

• Open your external email client and add a new account. 
• Choose Outlook.com or Exchange as the account type (do not choose manual IMAP). 
• When it asks for your email address and prompts you with the Microsoft login popup, enter your new @outlook.com alias and your normal password. 
• Because the system sees an @outlook.com address, it will correctly route you to the personal server, and the login will succeed! 

Once authenticated, your client will sync your mailbox normally, and you will still be able to send and receive emails using your beloved custom domain address. 

Please give this a try and let me know if the connection finally goes through. Hello [User's Name], 

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Answer 2

It sounds like you're experiencing issues with OAuth authentication for your Live.com email account, particularly with external email clients. Here are some steps you can take to troubleshoot this issue:

1. Check OAuth Configuration: Ensure that your email client is configured to use OAuth2 for authentication. If your account is set up for high volume email (HVE), make sure that the configuration aligns with the OAuth authentication requirements.
2. Expired or Invalid Tokens: If you have been using OAuth for a while, it's possible that the tokens used for authentication may have expired or are invalid. You may need to refresh these tokens or reauthorize the application.
3. API Permissions: Ensure that the API permissions requested by your email client match those allowed on the authorization server. Mismatched permissions can lead to authentication failures.
4. Basic Authentication: If you have disabled Basic authentication, be aware that some older email clients may not support OAuth for POP and IMAP. You might need to enable Basic authentication temporarily to access your account through those clients until you can resolve the OAuth issues.
5. Account Association: Since you mentioned that your account might be associated with both a work and a personal account, ensure that you are using the correct credentials for the intended account. Sometimes, confusion between accounts can lead to authorization errors.
6. Contact Support: If you continue to face issues, consider reaching out to Microsoft Support for assistance. They may be able to provide more specific guidance based on your account setup.

By following these steps, you should be able to troubleshoot and potentially resolve the authentication issues you're facing with your Live.com email account.

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References:

• Troubleshoot issues with high volume email (HVE) for Microsoft 365
• Can't connect to Outlook by using POP/IMAP and Modern authentication