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Michael McDowall

At what point would I migrate Echange 2007 (2008 SBS) to O365?

Hi,

I'm wondering what your advice would be on the timing of migrating Exchange 2007 to O365 from a 2008 SBS server?

Currently everything sits on the single 2008 SBS server. The plan is to migrate the AD, DNS,DHCP etc. on the 2008 SBS server to Windows Server 2019 and the Exchange 2007 to O365.

My plan was:

  1. Migrate AD,DNS,DHCP etc. to Windows Server 2019 but leave the Exchange 2007 running on the SBS which users would still use for now.
  2. This would leave me with a new DC (2019) and an old Exchange 2007 (SBS).
  3. Then I would create the ADSync to O365 of all the user accounts on the new DC. This would leave me at a good point for one weekend.
  4. Then the next weekend I would migrate all the mailboxes to O365 and decommsion the SBS 2008 all together. Then make sure all users can access emails with a new Outlook profile etc.
My worry here is once I transfer the FSMO roles the SBS server will stop working or may break Exchange 2007 running on it?
 
So I am wondering is the best plan to:
  1. Setup ADSync with the current SBS 2008. Sync all the AD users to O365. Then migrate the mailboxs to O365.
  2. Decommision the Exchange 2007
  3. Then migrate the 2008 SBS to Windows 2019
  4. Re-create the ADSync with the new Windows Server 2019 (I'm assuming this would all match up as the GUID would be the same for users?)
  5. Decommision the 2008 SBS
Hopefully that makes sense. Basically should I migrate Exchange first or last?
 
Thanks,
Michael
asked03/21/2019 13:35
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Last Activity 03/22/2019 17:30

1 Answer(s)

  • Mariette Knap

    Microsoft MVP

    Hello Michael,

    ADSync is not compatible with SBS 2008, see Azure AD Connect: Prerequisites and hardware | Microsoft Docs.

    Azure AD Connect cannot be installed on Small Business Server or Windows Server Essentials before 2019 (Windows Server Essentials 2019 is supported). The server must be using Windows Server standard or better.

    The best solution for this is to install Windows Server 2019 as a replica domain controller, leave the FSMO roles on the SBS 2008 and install Azure AD Connect on the 2019 DC. This means you can complete chapter 1 to 9 of How to migrate SBS 2011 to Windows Server 2019 Standard, Datacenter or Essentials without any issues.

    BTW, if you do a cutover to O365 as described here Cutover migration from Exchange Server 2007 on a SBS 2008 Standard to Office 365 you don't need to install Azure AD Connect but you can still do that as long as it is not on the SBS 2008

    answered 03/21/2019 14:05
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    Michael McDowall

    Perfect. Thanks for the reply.

    This question might be a bit stupid but do you have to move the FSMO roles first before migrating File Share, DHCP, Printers to the new server. My plan would now look like:

    Weekend 1 (Move as many services to the new DC as possible)

    1.  Add Win2019 server as DC
    2. Check replication of AD, DNS, GPO was successful
    3. Migrate File, DHCP, and Printers
    4. Setup  ADSync on Win2019 server - make sure AD accounts sync to O365 correctly
    Weekend 2 (Migrate mailboxes and decommsion SBS)
    1. Update Exchange 2007 version
    2. Staged migration of mailboxes to O365
    3. Move FSMO roles from SBS to Win2019
    4. Demote and decommision SBS
    5. Make sure users can access emails with new Outlook profie
    So the only major difference to your tutorial is Step 10. 'Transfer the operations master roles from the SBS 2008 to the Windows Server 2019 server' will now be done at the end after the migration of DHCP, Files and Printers. Will this have an adverse effect?
     
    Thanks,
    Michael
    Mariette Knap

    Moving FSMO roles does not have any effect so you can move it at the very end of the migration, just before chapter 16. The reason I do it earlier is that I want to see the server run happily after the move. Make sure you run the checks for replication health after you move the FSMO roles. Do not rush the demote process.

    replied 03/22/2019 17:30
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    replied 03/22/2019 13:08
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