Hotmail Email did not xfr to Outlook -

Here is a number you can try Toll free: (877)-274-4349

If they can't help maybe they can point you in the right direction. Good Luck!

Hotmail and Outlook would be the same address. Hotmail transitioned to Outlook quite awhile ago and his email address would have been transitioned to Outlook. But the way you're putting it makes it sound like he created a second GT using the same email
address. Because the Hotmail email address is the Outlook account. Is that correct? Has your friend contacted support at all?

Is the email address a live.con or hotmail or outlook address?

I'm sorry to hear that! What wall did you come to when trying the Alias method?

Edit: Is your new email a Microsoft Email? (ie: outlook, msn, Hotmail) ?

Since outlook is already a Microsoft server email it is not possible to use the outlook email you can add another email alias that is not a Microsoft server email (@outlook.com, @live.com, @msn.com) or you can create a new outlook email in the process of
adding an alias to the account at account.live.com/addassocid and it will put that new outlook account on the hotmail account or you can use any non MS email account.

Now keep this in mind you can have multiple aliases that you use to sign into accounts with (if they are not already a Microsoft account)

If you do add a new alias to your hotmail account and decide to remove your hotmail email from the account that will render the hotmail account null and void and you will never be able to get it back.

so do not remove the hotmail email from the account if you ever think you will need it for anything in the future