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Migration from Exchange 2010 to Office 365

Posted on 2014-09-30
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Last Modified: 2014-10-27
I wanted to see if anyone had done a successful migration from Exchange 2010 to Office 365. As usual Microsoft has bad documentation and nothing is very straight forward.  We are wanting to to integrate AD and SSO on as well into the picture and that is definitely not straight forward so if any one has done it successfully and has some good pointers that would be great.  Oh, our AD environment is 2008 R2.
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Question by:DaveKall42
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by:Robby Swartenbroekx
Robby Swartenbroekx earned 250 total points
ID: 40353345
How many users?
>1.000 -> hybrid migration is your only option
<=1.000 ->
   migrating in stages -> hybrid migration
  migrating everyone at once -> cut over migration over Outlook Anywhere

Hybrid = Dirsync + ADFS
Cutover = first start the migration in office365, than setup dirsync with password synchronisation
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torns tenkristen earned 250 total points
ID: 40354234
Beside the above suggestion, I would like to refer at Exchange server deployment assistant that is available from Microsoft and provides a complete road-map by checking all the required prerequisites to achieve this goal in right direction. Please walk through given link : http://technet.microsoft.com/en-us/office/dn756393.aspx
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by:DaveKall42
ID: 40367287
How well does SSO work with office 365?  Is it worth setting up?  Can you only do SSO and LDAP integration with a hybrid  model or does that work with cutover as well?
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by:Robby Swartenbroekx
ID: 40367970
Real SSO needs ADFS + Dirsync and a hybrid setup.

With Dirsync with password sync (possible with the latest Dirsync), you don't have a real SSO, but it looks like it, and it is usable in a cutover setup.
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by:DaveKall42
ID: 40378157
So this might be a stupid question but with the cutover process is there a point where I can prep the migration and not affect the current install of exchange and users and then do the cutover migration?  Are there any docs you would recommend about setting up dirsync?
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by:Robby Swartenbroekx
ID: 40379449
not a stupid, but actually a very good question.
On technet there is a decent how to: http://technet.microsoft.com/en-us/library/jj874016%28v=exchg.150%29.aspx to use as a guide.

We setup a trial account, make Outlook anywhere work on the on premise server with a real certificate (I use mostely startssl, where you can generate a free certificate), but there are also other CA's that have free trial certificates for 30 to 90 days.
Then we do the migration according to the Technet document
then you can setup dirsync
and finaly you take a point where you instruct all users to stop mailing on the old server, you change the mx records, do a final sync, and configure the client machines.

We mostely have sites with 10 to 25 users, but databases vary from 10Gb to 100Gb all with none to almost no problems. We are now planning our biggest until now with 75 users and about 200-250Gb of data, our biggest challange is to keep the actual migration as short as possible and see how we can configure all those clients without congesting the internet line when they all try to download the offline copies.
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by:torns tenkristen
ID: 40379496
As suggested above, you may follow the steps mentioned in Exchange server deployment assistant that is available from Microsoft. It provides a complete road-map to accomplish migration goal by covering all the required prerequisites.

Also, please take a look on this well explained article that could be a good start-up in your circumstance while need to migrate from exchange 2010 to Office 365 : http://help.outlook.com/en-us/140/Ff628719.aspx
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Author Comment

by:DaveKall42
ID: 40380245
I guess I am wondering, can I move everything to the new server before the users start using office 365 and continue to use the old in house exchange server? Also, does the certificate need to have autodiscover.<domain> as the fqdn or can it be any name?
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