A new essentials server and a move to office 365 from POP.  What order woudl you recommend?

BeGentleWithMe-INeedHelp
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Looking to replace an SBS 2003 install with an essentials 2012R2 install AND move the 6 users from hosted POP mail to office 365 exchange.

The SBS 2003 has not been using Exchange - no shared calendar / contacts / folders.  Just users using pop email and conjtacts stored locally in the PST.

What order would you do things?  Install the server then once that's all set, move to office 365?  Or better to do them concurrent (I haven't used Essentials before, but heard that it 'works' with office 365?  So is it better to set it up from the start for office 365?

Office 365 first then the server?
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Distinguished Expert 2018
Commented:
I would do the server then O365 personally. SBS 2003 is near dead so I'd make that the priority. You can enable the essentials O365 integration after you've moved to O365. It isn't anrequirement to enable it during server setup?
David AtkinTechnical Director
Top Expert 2015
Commented:
Depending on the amount of users. I'd probably do this all at the same time.

Setup the server and office 365 integration before taking the server to site or making it live. Switch the MX records to the office 365 once you have the server on site and the computers connected. Bear in mind that DNS can take a little while to update (depending who your with).

We tend to do installs on a weekend to make the transition smoother for the end users and generally quicker.
David AtkinTechnical Director
Top Expert 2015
Commented:
Just re-read the question. As you've got 6 users I would do it at the same time.

Essentials is designed to work with office 365 really well. It's relatively straight forward to push up users to office 365.

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