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Migration to Office 365 questions

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I work for a school that currently use Live@edu and want to move to Office 365.

Currently the students have SMTP addresses and mailboxes in Live@edu, for example They use ILM to sync to Live@edu now.  The teachers use on premise exchange with an SMTP address of with the intent of moving to Office365 and keeping the SMTP address.  The UPN for all users right now is in the on premise AD.

With Office365 it is my understanding that if I want the students to sync to and teachers to that the UPN/Proxy Address/Email Address of the on premise AD account need to match.

Is that a correct assumption?

Is there any way to not change the UPN and just rely on the email address and still have SSO using ADFS and dirsync?


If a change is necessary on the on premise domain I question how this will affect some of our applications.  Or will it if the the is just an added UPN to the domain?


Is there anything I'm missing here?

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