I have a customer I am trying to migrate off of SBS 2008. They are using the Exchange Server. I did a cutover migration to Office 365 that went about as well as it possible could but am having fits redirecting their Outlook clients to Office 365. I can manually configure Outlook to point to Office 365 but every time I reboot the workstation Outlook winds up pointing right back to their Exchange Server. I cannot keep it pointed at Office 365. The autodiscover keeps changing things back to their Exchange Server. Any idea how to point Outlook to Office 365 and make it last?

BTW their Outlook is a mix of 2010 and 2013


Once the migration is complete, you need to stop the exchange server, otherwise autodiscover will keep pushing clients to the exchange server.

The basic steps are:
1. Setup Office 365 accounts
2. Change the MX records so new mail is redirected to the new location.
\!/ at this point, they will stop getting mail in their inbox.
3. Export all mail from the old exchange server to PST files
4. Stop the exchange server
5. Setup new profiles in outlook
6. Import old PST files.

If the organisation is huge, different strategies may be required, but the overall process remains the same.

  • Well.... the Exchange migration was done with a cutover migration. I asked about stopping or even uninstalling Exchange at that point and was told it could be very detrimental to SBS 2008 to either stop all the exchange services or uninstall it. Have you tried it on a SBS2008 before? – Refurb Apr 30 '18 at 20:33
  • Yes, on one of our customers where we migrated them from SBS2008 to Office365, we stopped the exchange services. We didn't uninstall them as we were not sure how that would work in a Small Business Server environment, but I know you can also uninstall WSUS on SBS so exchange should not be that different. – LPChip Apr 30 '18 at 21:12
  • Did you have the same problems configuring Outlook on the workstations until you stopped the Exchange Services? I would prefer not to uninstall Exchange in case something goes wrong.... – Refurb May 1 '18 at 14:44
  • Yes I had. Stopping the exchange services then creating a new outlook profile was the way to go. Note, just stopping the services is not uninstalling Exchange. You can start the services again and revert back. – LPChip May 1 '18 at 19:36
  • I think I over thought this one. After manually configuring Outlook to point to Office 365 I kept getting a pop-up about allowing autodiscover-s.outlook.com/autodiscover/autodiscover.xml to configure Outlook. I thought it was the Exchange Server trying to re-configure Outlook. As it turns out it was from Office 365. As soon as I allowed it... it reconfigured Outlook yet again (over-riding my manual programming) and life was good. Nice to know I can stop the Exchange Services if I need to. Thanks for the help. – Refurb May 2 '18 at 20:40

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