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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 student@ol.abc.k12.us. They use ILM to sync to Live@edu now.  The teachers use on premise exchange with an SMTP address of @abc.k12.us with the intent of moving to Office365 and keeping the @abc.k12.us SMTP address.  The UPN for all users right now is @abc.k12.us in the on premise AD.

With Office365 it is my understanding that if I want the students to sync to ol.abc.k12.us and teachers to abc.k12.us 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 ol.abc.k12.us is just an added UPN to the domain?

 

Is there anything I'm missing here?

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