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New Friend (or an Old Friend who Built a New Account)
Posts: 79
Reply with quote  #1 
The starting point is an Exchange 2010 SP3 environment (all on premises currently).

Note: this is a completely different environment from the one those with a good memory may remember from the old forum (Just in case someone asks "I thought you were going to...?").

We are contemplating a move to either Exchange 2016 (on-premises) or Office 365 / Exchange Online (just the Exchange product) or both.

In the very last case then (the "both" option), we would have a hybrid Exchange environment.

Moving to either Exchange 2016 or Office 365 requires the extension of the Active Directory schema.

If we selected the "both" option, should the schema be extended for Exchange 2016 first or for Office 365 first?

I'm not aware of the existence of a preferred order but thought I would ask here.

Has anyone gone this way?

How did you proceed?


Posts: 465
Reply with quote  #2 
Please do verify this,,, dont let this be a hurdle...

Office 365 – Why Your UPN Should Match Your Primary SMTP Address


Tim Bolton @jsclmedave
Email: [string](0..20|%{[char][int](32+('527377347976847978324785847679797514357977').substring(($_*2),2))}) -replace ' '  

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Senior Member
Posts: 300
Reply with quote  #3 

as far as I am aware (but it may well be I am missing something) there is no separate process for extending schema for O365. You just download Exchange and run setup /ps. This is the same step you would be doing if you were to install Exchange on premise.

Organization preparation is a different question. You don't need to prepare your AD forest for Exchange if you go cloud-only so you just do it before deploying Exchange on premise IF you decide to do it.

Evgenij Smirnov

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Associate Troublemaker Apprentice
Posts: 896
Reply with quote  #4 
First off, look at the economics of the move.
On Premise Exchange costs X
Office 365 costs Y.
Do you know what X and Y are?
I have a simple excel sheet I can share if you wish that will give some indication of comparison costs.

With regard the change/ Schema upgrade, do whichever you hit first.

Have you tried turning it off and walking away? The next person can fix it!

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New Friend (or an Old Friend who Built a New Account)
Posts: 79
Reply with quote  #5 
Thanks to all for the input, both here and via chat.

Joe: sure, if you want to sent me the spreadsheet, that would be great.

I think you have personal email address?

If not, I'll try to send you a message. I'm pretty sure I have yours'.
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