SBS 2003 Exchange to Office365 Migration

I'm gearing up for migrating about 30 users from exchange 2003 (sbs 2003) to Server 2012 R2 Standard + Office365.

Information store is 130GB. (I have spent nearly a year restarting it every night to keep it running.)

Internet upload speed is usually 7-8Mbps as per speedtest.net

There seems to be lots of info about specific stages, but I'm finding it difficult to piece everything together in a coherent picture that is relevant to this situation.

The old server is functional. The new Server is up and running on the same network although DHCP is disabled and domain and users are not configured.

Stations are still logging into the old domain.

I want to migrate the Exchange over using the cutaway migration method, as manually uploading PST's could take days and then I'd have to cleanup the items in the gap after.

Question #1 I want to use DirSync and Single Sign-on. One source seemed to indicate that Dirsync cannot be used if you've done a cutaway migration. Is this still accurate? Can anyone verify this either way?

Question #2 I want to change all of the usernames from First initial.Lastname to FirstnameLastname which is the same as their e-mail address format. Can this be done after moving to Office 365 or should it be done before?

Question #3 Does the new on premise domain controller domain name matter? Does it need to be related to their external mail domain? Should it be the same as the old domain?

(currently is domain.com for e-mail domain & domain.local for internal)


Thankyou for taking the time to read this!
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MJCSAsked:
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Vasil Michev (MVP)Commented:
1) Dirsync cannot be used for cutover migration. You CAN however use if after you migrate the mailboxes and stop the cutover batches. Trust the TechNet documentation: http://technet.microsoft.com/en-us/library/jj874016(v=exchg.150).aspx

I hope you dont mean deploying AD FS, for 30 users this is a bit of overkill. Using dirsync with password sync should be the best solution, so if this is what you mean by SSO, you will be able to implement it.

2) Can be done after, but if you are going to use dirsync you will need to start preparing for it accordingly. So you might as well change things up front. Read this article for more details: http://technet.microsoft.com/en-us/library/hh852478.aspx

3) No, but it's best to be something routable if you want to keep things simple. You can have a .local domain and simply add another routable suffix, domain.com in AD, no problems there.
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MJCSAuthor Commented:
To clarify point #3:

Do you mean

domain.local.com?
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Vasil Michev (MVP)Commented:
No, it should be just domain.com in your case (the example you gave in the original post). In principle it doesn't matter that much, you can have domain.local as well. But if you are going to use dirsync, you will have to make sure that the UPN of the users is in the form user@domain.com (where domain.com can be resolved from outside of your network).

So either use domain.com from the get go, or simply add domain.com as additional suffix later. Failing to do this will result in all the users getting UPNs in O365 in the form of user@domain.onmicrosoft.com.
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MJCSAuthor Commented:
So if I use domain.com internally, do I need to worry about any DNS config  changes? or is the domain.com internal simply cosmetic/ for consistency?
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Vasil Michev (MVP)Commented:
It will just make it a bit easier when switching to O365. But it's not mandatory.
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