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I have a address that was used to connect to my Windows 8 local user account. This is the account that shows up in the Users app, as well as on the lock screen.

I also have an aliased that I would like to use instead as the login name is nicer. Is it possible to change the app to use the alias instead? When I tried to log in during setup with the address it told me to use the master address instead.

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I'd recommend switching to a local account first:

After that has been done sign in with your new hotmail account.

I should also note that any purchases made in the old account will not be transferred over (99% about this)

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You have to wait unless Hotmail itself is migrated to Outlook completely. Till that time, the answer to your question is no

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