Terminal Server Clone 2008 R2 - 2012 R2 (User Profile Retention)

Good Morning All,

I am in a situation where I am attempting to migrate a terminal server from 2008 R2 to 2012 R2.
The server is virtualized (ESXi 6), to avoid downtime, I have cloned the server with a new MAC.

The machine has been fully upgraded to 2012 R2, however after renaming and re-joining to the domain,
I am of course greeted with new profiles for domain accounts that have previously logged into the server.
I'm looking for a free or paid way to mitigate this.
(I should note, this is a copy of the old terminal server, all data is retained (user folders - C:\users)

Is there a way to, without user interaction, merge the new and old profiles?
I am especially interested in retaining profile specific registry settings relating to Outlook.

Thank you in advance
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Alex GreenProject Systems EngineerCommented:
If you have your old terminal server, you can use robocopy to move the profiles over I guess, actually, I don't think that'll work since you have a new profile layout on 2012.

You'd have to use the profile migration tool,

http://www.forensit.com/downloads.html

https://www.experts-exchange.com/questions/28702099/Best-way-to-migrate-profiles-from-Windows-Server-2008-to-Windows-Server-2012-both-Remote-Desktop-Servers.html

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Alex GreenProject Systems EngineerCommented:
But I think the best option is the last one, set up a remote terminal services profile location, get them to log onto the 2008r2 box, then overnight migrate to 2012 and then get them to log on, it'll convert it automatically at that point and give them a V2 profile.
Leverage IT Group, LLC.Author Commented:
I believe the forensit tools may do the trick.
Do you know if the user needs to have logged onto the new server, before running the profile migration tool?
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Alex GreenProject Systems EngineerCommented:
No they shouldn't be logged in, if they are logged in you can't move the profile since it's in use (From my understanding).

Unfortuantely you'd need to check the application itself, i've not used it before.

Regards

Alex
Leverage IT Group, LLC.Author Commented:
Ended up using the Forensit profile manager.
I'm able to re-assign the profiles to the respective AD accounts.

I appreciate you pointing me back in that direction, sometimes you can use a tool and then completely forget that it exists.
Leverage IT Group, LLC.Author Commented:
Alex reminded me of the Forensit toolkit.
This is exactly what I needed
Alex GreenProject Systems EngineerCommented:
:-)

You're welcome, anything else you know where we are.
Shaun VermaakTechnical SpecialistCommented:
Did you rejoin the same domain? If so it would be weird that you get new profiles
Alex GreenProject Systems EngineerCommented:
I don't think he had remote terminal services profiles in AD so it didn't know where to pull them from.
Shaun VermaakTechnical SpecialistCommented:
So in theory a profile image list repoint could also work because the ACLs are correct
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Windows Server 2012

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