Migrating Mailboxes from SBS 2008 to Office 365

My customer has a SBS 2008 Server and uses the built-in Exchange Server 2007. I migrated their mailboxes to Office 365 via a cutover migration. Now comes the impossible part. Their workstations are a mix of WIndows 7 and WIndows 10. Outlook on those workstations is a mix of 2010 and 2013.

   I can manually configure their Outlook to point to Office 365 but it will only stay for maybe 4 hours and reverts back to their Exchange Server. Simply opening Outlook and letting it sit it reverts back. I can tell when the Outlook 2010 workstations revert back because a pop-up asking for their email address and password keeps popping up. I can tell when the Outlook 2013 workstations revert back because they get a pop-up stating  "the microsoft exchange server administrator has made a change that requires you to quit and restart outlook". At that point Outlook has reverted back to pointing to their Exchange Server.

   I have tried stopping all the Microsoft Exchange services on their Exchange Server. Nothing I have tried works. I cannot keep Outlook pointed to Office 365. It keeps automatically reverting back. My guess is that I need to change the autodiscover services on the Exchange Server but that is just a guess. Does anyone know how to do this?
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LockDown32OwnerAsked:
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zvitamConsultantCommented:
you have to do as follows:

For every workstation:

1. Backup the mailbox contents into a local PST.
2. Create a new outlook profile and connect it to the office 365 account.
3. copy the contents of the saved PST into the new profile.
4. Leave the otlook open for a few hours to let the mailbox contents sync to the office 365 cloud.

Hope that helps,
Zvitam.
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LockDown32OwnerAuthor Commented:
That won't do it. The cutover migration does the same thing as exporting/importing the PST. When I do this I always delete and create a new profile pointing to Office 365. The problem.... after being open for about 4 hours Outlook reverts back to pointing to their Exchange Server.
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Cliff GaliherCommented:
You HAVE to Uninstall exchange (which will break SBS so you might as well migrate off that as well.) There are objects in AD that Outlook looks for (DNS Autodiscover is actually a fallback mechanism) and you'll keep hitting this as long as exchange exists. Uninstalling exchange removes these AD objects.

There are powershell commands to update the object attributes to work with O365, but exchange 2007 can be a little glitchy (2010 was much better) and SBS tends to reset them (unique to SBS.)

Trying to get SBS to coexist with O365 is never going to end well. As it happens are parts of SBS are out of extended support and officially end of life anyways so this is a good reason to kill it off altogether.
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Jose Gabriel Ortega CCEO Faru Bonon ITCommented:
Step 1, get a middle server migration for exchange 2010.
Then do the cutover migration from 2010 to exchange online.
You have 120 days to do this (free version of exchange)

And SBS is very bad as a starting point for any migration (AD or Exchange), it doesn't like to share resources with any other server.
To start in a good shape you need to get rid SBS after migrate (AD and Exchange to a new server), since you're going to move everything to the cloud it would be a Temporarily server.
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LockDown32OwnerAuthor Commented:
For anyone else who happens across this thread here is the definitive answer. The Exchange Server remains un-touched. You need to edit the registry on the workstations (user profiles). When this is done autodiscover will connect to Office 365 and not the local Exchange Server:

Outlook 2016 replace XX.X with 16.0
Outlook 2013 replace XX.X with 15.0
Outlook 2010 replace XX.X with 14.0

REG ADD HKCU\Software\Microsoft\Office\XX.X\Outlook\AutoDiscover /v PreferLocalXML                   /t REG_DWORD /d 00000000
REG ADD HKCU\Software\Microsoft\Office\XX.X\Outlook\AutoDiscover /v ExcludeLastKnownGoodURL          /t REG_DWORD /d 00000001
REG ADD HKCU\Software\Microsoft\Office\XX.X\Outlook\AutoDiscover /v ExcludeExplicitO365Endpoint      /t REG_DWORD /d 00000000
REG ADD HKCU\Software\Microsoft\Office\XX.X\Outlook\AutoDiscover /v ExcludeScpLookup                 /t REG_DWORD /d 00000001
REG ADD HKCU\Software\Microsoft\Office\XX.X\Outlook\AutoDiscover /v ExcludeHttpsRootDomain           /t REG_DWORD /d 00000001
REG ADD HKCU\Software\Microsoft\Office\XX.X\Outlook\AutoDiscover /v ExcludeHttpsAutodiscoverDomain   /t REG_DWORD /d 00000001
REG ADD HKCU\Software\Microsoft\Office\XX.X\Outlook\AutoDiscover /v ExcludeHttpRedirect              /t REG_DWORD /d 00000000
REG ADD HKCU\Software\Microsoft\Office\XX.X\Outlook\AutoDiscover /v ExcludeSrvRecord                 /t REG_DWORD /d 00000001
REG ADD HKCU\Software\Microsoft\Office\XX.X\Outlook\AutoDiscover /v ExcludeSrvLookup                 /t REG_DWORD /d 00000001
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