Change mailbox email address of disabled user to alias of another user.

I have an executive user that is setup with 2 accounts, one that his assistants could access and one that is private.  He moved to a different role in the company and no longer wishes to have a separate private account.  I disabled the private
account and the mailbox added the address of the private account as an alias to his regular account.
My Outlook users are getting NDRs when sending to the private address.  It goes through when using OWA and emails from outside users.
How do I fix this?

Yes, I assumed that to be the case as well.  I should have mentioned that I tried that already on 3 different user account.  I am not sure how the OOF would work after the mailbox has been deleted.
To fix it I had to delete the nickname cache entry then close and reopen Outlook before testing it.  If you don't close and reopen Outlook before manually typing the address into the To field it re adds the incorrect entry to the nickname list.
There should be a way to remove a nickname list entry for everyone since it resides on the server.

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