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Migration Mode SBS 2008 to 2016 Essentials

Migrating SBS 2008 to 2016 Essentials using 'Migrate Windows Small Business Server 2008 to Windows Server Essentials"
https://docs.microsoft.com/en-us/windows-server-essentials/migrate/migrate-windows-small-business-server-2008-to-windows-server-essentials

The server is a Dell with 2016 Essentials pre-installed with the Essentials role, it was not configured as a domain controller.

In the above document I'm stuck at Step 2: Install WSE in migration mode https://docs.microsoft.com/en-us/windows-server-essentials/migrate/install-windows-server-essentials-in-migration-mode
I don't have an option to install in Migration Mode, how do I get to that point?

I have installed a few SBS 2011 to WSE2012R2 but not SBS2008 to 2016, I would rather migrate than setup a new domain.

Thanks
SBSWindows OS

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Darren Wood

8/22/2022 - Mon
Lee W, MVP

You cannot have it pre0installed and install in migration mode.  You'll need to re-install cleanly in migration mode:
https://docs.microsoft.com/en-us/windows-server-essentials/migrate/install-windows-server-essentials-in-migration-mode
dpacheco

ASKER
That's what I was thinking, thanks.
dpacheco

ASKER
I booted from the DVD, formatted the boot partition and installed but no option for migration mode. What am I missing?
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William Peck
Cliff Galiher

Migration mode onky existed in 2012. It was gone by 2012 R2.
dpacheco

ASKER
So I cannot migrate and must setup a new domain?
Cliff Galiher

You can migrate. There just isn't a migration mode. You essentially install essentials, but before running the post install wizard, you join an existing domain THEN complete the post installation wizard.
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Cliff Galiher

Official documentation. Says 2016 R2, but applies to 2016.

Yes the previously linked docs also say 2016, but that is wrong and has been repeatly reported as documentation bugs to Microsoft.  But there seems to be nobody left in the essentials team left to fix it.

https://docs.microsoft.com/en-us/windows-server-essentials/migrate/migrate-from-previous-versions-to-windows-server-essentials-or-windows-server-essentials-experience
dpacheco

ASKER
I saw this document as well but since there was one labeled migrate 2008 to Essentials...
Once I've added this server to the domain, I finish the post install wizard and then the Transfer operations master roles?
Cliff Galiher

The document covers the steps in detail and the correct order.
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dpacheco

ASKER
I joined to the domain and when I go into the configuration
Wizard it says this has been setup as a domain member, I hit next and login as my domain admin, stops and says restart, I have done twice but same thing. The domain administrator a member of the groups listed.
Ideas?
Cliff Galiher

Not off the top of my head. The documentation is accurate if followed exactly. I've done in with many 2012 R2 installs and a dozen or so 2016 installs. But if not followed, odd things can obviously happen.  I couldn't guess what though.
dpacheco

ASKER
This is a problem I remember on one of my first 2012 migrations but I'm not getting the errors in the event log that pertain.

Maybe I'm reading this wrong but it would seem to me that I have to finish the configuration before I can transfer the FMSO roles. If I try do try to run NTSDUTIL from the destination server is says can't find the file and the instructions clearly say to run it on the destination server.
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Tom Cieslik

dpacheco

ASKER
That is what I'm following
Tom Cieslik

So I don't understand where you've stuck ?

Step 2 is:
Step 2: Install Windows Server Essentials as a new replica domain controller. This section describes how to install Windows Server Essentials, or Windows Server 2012 R2 Standard (with the Windows Server Essentials Experience role enabled) as a domain controller

There is not such of :Migration Mode
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dpacheco

ASKER
That is where I'm stuck, it has been joined to the domain and I'm running the post-deployment configuration, it just says
Please restart the server, and then run the configuration wizard again. If the issue still exists please refer to the help link for more troubleshooting  steps. The link is useless. http://go.microsoft.com/fwlink/?LinkId=296659
Cliff Galiher

You can try promoting the machine to a DC manually. The essentials wizard is supposed to do this if it is joined to a domain already, but I've seen situations. Especially if the source server wasn't "clean" first. A lot of folks skip the BPA checks from step 1.

You can install the ADDS role. Promote to DC. Then complete the essentials wizard. That usually "unsticks" mild mistakes.
dpacheco

ASKER
I did run the BPA on the source server which came out with no issues except WSUS not working, it was disabled a while back. I don't see anywhere that's telling me to raise the forest functional level? I did not see anything about this but remember having to do it  for SBS2011.
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Steve

Unfortunately the wizard doesn't provide much help on this as you've seen. The event log is the only place you can narrow it down really.

Take a look in the system & application logs at the the you ran the wizard and see what is there. This usually narrows the search down and lets us assess the best way forward.


In general, there are a number of reasons this generic 'please restart and try again' message is being thrown. In many cases it's due to some previous SBS customization that the wizard isn't expecting.

Best path is usually to add to domain, promote to DC, make sure replication is working and move FSMO roles across.... THEN run the wizard.



Notes on SBS customization:
SBS (and essentials) is a pre-configured package. If you customize it in a way it wasn't intended it can make things much harder.
Examples include removing/disabling elements (exchange, WSUS etc.), creating child domains, using ADSIEDIT to make changes etc. etc.
SBS is a very carefully configured mixture of applications that were never really intended to be running on a single server, so making changes can have unexpected results.
dpacheco

ASKER
I have looked at the event log, I get a user device registration error and dcom error and group policy errors, these after I joined the domain.

At this point I'm thinking it might be best to not migrate and setup the server as new with a different domain. It will be more work to create new profiles but cleaner. They are on Office 365 so no exchange migration. Will I be able to have the 2 domains on the network at the same time without issue? It will be done well before 21 days,
dpacheco

ASKER
These errors do not occur when I run the wizard but when I login, there are no errors when I run the wizard. I can fix the group policy issue but I'm still thinking new domain. There are only 6 users, creating new profiles are a pain but that may be better. Opinions?
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Steve

With only 6 uses it’s certainly worth considering starting new.
As long as you stay within the time limits it will work fine with both on at the same time.
Question: is your o365 tied to your AD? May be affected if it is.
dpacheco

ASKER
No, O365 not tied to AD.
Steve

Worth considering then. not many users to migrate and it may be a change to cleanup and fiix any old issues hanging around.
Did you used to use exchange and you've migrated to o365?
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dpacheco

ASKER
Yes.
I'll finish this up tomorrow, luckily most users off this week.
dpacheco

ASKER
I appreciate everyone's comments and help, there was no solution to the initial question since I opted to not continue troubleshooting and setup a new domain. Thank you!
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Darren Wood

you will have to migrate as you would any other domain upgrade. By upgrading the schema to support a 2016 domain controller. Up date the domain then add the 2016 server and put that to a domain controller. then carry on with the Microsoft Documentation for the migration. I have done many SBS server migrations over the years and that's the way I do it to 2016, after first migrating all the mailboxes to office 365.
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