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Office 365 Cutover Migration with Outlook

Posted on 2014-09-11
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Last Modified: 2014-10-03
We have completed the sync portion of our exchange 2010 migration to Office 365 and are now ready to move into the cloud. I have a few questions which I have not found satisfactory answers to; if anyone can provide clear answers, I'd appreciate it.
- The best way to set up the new Outlook profiles. We have 175 users who need to have their Outlook and Iphone accounts switched. The prevalent answer is to do them one at a time manually, Clearly this is not a desirable approach! Surely their must be some kind of group policy or migration tool solution?
-We will be setting up Single sign on and syncing with our local Active Directory. The advice on the guides I've read is to keep a local copy of Exchange running with this solution. Why? Is this necessary? Do I need to have all the users licensed a second time? Can we do without it?
-Finally, assuming we can get all the profiles switched over, are we going to experience huge slowdowns while all the accounts sync out of the cloud the first time everyone logs in?

Hope these questions make sense. Thanks again for the help.
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Question by:JP_TechGroup
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by:Vasil Michev (MVP)
Vasil Michev (MVP) earned 250 total points
ID: 40318665
1) Outlook uses autodiscover for the 'automatic' configuration, the best you can do is turn on the "Automatically configure profile based on Active Directory Primary SMTP address" GPO setting. The process however will not be fully automatic. You cannot just pre-populate all the relevant settings, as with Exchange 2013 the connection process has changed and getting the correct settings for each user will cost you a lot of additional effort. Just stick to autodiscover. And, in domain environment with existing Exchange on-prem, you might consider disabling the lookup for the local server: http://support.microsoft.com/kb/2212902

2) It's not mandatory, however with dirsync you will have to edit any (even Exchange related) attributes on-prem. Removing Exchange will remove the 'convenient' tools for doing this, but you will still be able to edit them with dsa.exe, etc. Also, DG membership will be a bit more trickier, read here: http://support.microsoft.com/kb/2417592. If you are fine with those points, just remove it completely.

3) You can have the two accounts running side by side in Outlook for some time, otherwise it will of course need to sync the full copy of the mailbox. Still, having them both can also cause some trouble, such as constant autodiscover prompts, etc.
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by:Jian An Lim
ID: 40326954
you have chosen a cutover method. it really means every users need to be involved to manually change their settings. Cutover also means all ost file will be re-created.

so disable autodiscover locally and globally (dns changes and registry hack) make the changes of exchange user to mail-enabled user then let the users re-discovered.

the idea is yes, it might be, but BITS should kicks in to sync the remaining, just have to brace the impact of organised users working from home. The is one of the biggest disadvantages for cutover method but really depends on size. how many GB you have uploaded? (i.e. this size will be redownload on the switch over day)

p/s: remember to switch the mail-enabled user when it is ready.
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http://community.office365.com/en-us/w/exchange/835.cutover-exchange-migration-and-single-sign-on.aspx
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by:JP_TechGroup
ID: 40342447
Sorry for the long delay in response. Just a few more questions.
We have set up a dedicated 2012 server to handle disync and Exchange.
When we decommission the existing Exchange server after the cutover is complete, how do we syn this copy of exchange with Office 365 for admin purposes.

Disabling autodiscover will not prevent Outlook from opening or trying to open the existing user profile. In order for this too work, a new profile has to be created. Is there some way to instruct Outlook to disregard the users profile and re-run the startup wizard when the user opens outlook? Thanks.
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by:Vasil Michev (MVP)
ID: 40342521
With cutover migration you will need to configure a new profile indeed, that's where the autodiscover bit comes. And it's best to keep the existing profile for a while, just to be sure that users dont loose any important items that might have not been migrated. Best option is to convert the mailboxes to mail-enabled users (after you are confident that all went well with the migration).

As for decommissioning Exchange, it's advisable to leave at least one box active. It will help you with the administrative tasks. You can remove all the other servers as needed, decommission the roles and remove the mailboxes/storage at a later date.
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by:JP_TechGroup
ID: 40342854
>With cutover migration you will need to configure a new profile indeed, that's where the autodiscover bit comes. <
I understand that, but maybe I am not understanding the point of disabling autodiscover. I created a test OU and applied a GPO to it that disables all 5 roles of autodiscover, then added user with a previously setup outlook profile to that OU and logged in. The user has can open outlook as usual and their old profile opens. True, if I test autodiscover, if fails, but so what? We want to have their old profile be ignored and have the setup wizard re-present itself to the user, yes?
Thanks.
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by:Jian An Lim
ID: 40342924
Hi,
the old profile will keep open as the old mailbox is still exist, it will only do another round of autodiscover if you disable the mailbox hence it will have to force to re-create a mailbox (manually) (but with autodiscover, the configuration will be a few click a way)
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LVL 38

Expert Comment

by:Vasil Michev (MVP)
ID: 40343255
Because you need to add the new profile, it will perform an autodiscover lookup and it will query the local Exchange server first. Check for example step 6 in the following article: http://technet.microsoft.com/en-us/library/jj874018(v=exchg.150).aspx
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by:JP_TechGroup
ID: 40343827
Not to labor the point, but I why then would i want to disable auto-discover? Once users are converted to mail enabled users, don't we want auto-discover to run?
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Jian An Lim earned 250 total points
ID: 40345232
we are not saying you need to disable any auto-discover

both autodiscover will be running, you just need to make sure the outlook contact the office 365 autodiscover first rather than your local exchange server.

and outlook behaviour

First -> SCP Lookup
Next -> https://<smtpdomain>/Autodiscover/Autodiscover.xml
Next -> https://autodiscover.<smtpdomain>/Autodiscover/Autodiscover.xml
Next -> http://autodiscover.<smtpdomain>/Autodiscover/Autodiscover.xml
Next -> SRV record query for _autodiscover._tcp.<smtpdomain>

What you need to do is to disable certain outlook behaviour so they use the autodiscover rather than SCP or SRV

(or you change your internal SCP record but that means you will break the internal users)
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by:JP_TechGroup
ID: 40346148
>so disable autodiscover locally and globally (dns changes and registry hack) make the changes of exchange user to mail-enabled user then let the users re-discovered. <
Yes, you are!
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by:Jian An Lim
ID: 40349210
okay, my apologies, when i say disable autodiscover, i really mean disable the SCP and change the autodiscover so it is not easily.
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Author Comment

by:JP_TechGroup
ID: 40350491
Ok, I think i've gotten turned around in circles here!
What are the steps necessary to complete this migration as it pertains to Outlook once I have completed my migration on Office 365 and updated my DNS records and what behavior can I expect from Outlook once this is done?
Will the user see the wizard when they try to open Outlook or will I need to creat a new profile for them manually?
Thanks.
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Author Closing Comment

by:JP_TechGroup
ID: 40359506
Well, it went... That's all I can say.
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