Migrate terminal server 2003 to 2008 R2

We currently have a physical terminal server 2003 which I want to migrate to a virtual 2008R2 terminal server.
I am wondering what is the best way to do this with a minimum of downtime.

Since this is not a DC, I should be able to do an inplace upgrade to 2008 R2 and then virtualise?
Or I can setup a virtual 2008R2 and migrate the user profiles, licenses to the virtual machine?
Any ideas please?
x2x2xAsked:
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VB ITSConnect With a Mentor Specialist ConsultantCommented:
You can't do an in-place upgrade for the Terminal Services role from Server 2003 to Server 2008 R2. See the description for Terminal Services in this table: https://technet.microsoft.com/en-us/library/ff972408(v=ws.10).aspx#BKMK_Server_roles

You also do not want to do a straight upgrade, it may be too much of a shock to the users.

Best way to do this would be to fire up the virtualized 2008 R2 Terminal Server alongside your current 2003 Terminal Server, install all your programs, then get a user or two to log in and test the new environment to make sure everything is working.

As mentioned above, there have been changes to the TS profile starting from Server 2008 where the roaming profile folder is now appended with ".v2". Here's a list of things to consider:

- Enable folder redirection for the Desktop, Documents, and Favorites folders
- Install 64-bit drivers if network printers are installed on a 32-bit print server (as 2008 R2 is 64-bit only)
- Ensure all the programs installed on the 2003 TS are compatible with 2008 R2
- Terminal Server License role needs to be running on a Windows Server 2008 machine at minimum (already mentioned above). You can install the licensing role on the 2008 R2 TS itself.
- Get each users login details and sign into the new 2008 R2 TS to do the initial profile setup - Outlook, printers, etc. etc.
- Take this as the perfect opportunity to redesign your Group Policies to lock down the environment (if required)

That's all I can think of for now but I'll let you know if I think of anything else. Hope the above helps.
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schmieguCommented:
There is no inplace upgrade to 2008R2 (and even if it were, I woudn't do it). And you need at least a 2008 TS License Server (2003 TS licenses aren't valid).
There was a change in the profiles, so I would let them recreate automatically. If your TS profiles are on a file server, you can keep the path - a Profile.v2 will be created and the old  settings will be imported.
Create the new 2008 RDS, test it and then rename the server (at least in DNS), so users will be connected to it.
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x2x2xAuthor Commented:
Thank you for the comments.
So the best way to go is the 2008R2 running next to the 2003.
Now since I need new TS licenses for that, I am thinking of upgrading to 2012R2 while I'me at it .... I guess that is the same procedure?
For the user profiles can I just copy them manually to the .v2 directory and import the registry settings?
HKLM\Software\Microsoft\WindowsNT\Currentversion\ProfileList   ?
Or better to do this via GPO, using the following guide?
http://support2.microsoft.com/default.aspx?scid=kb;EN-US;947025
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schmieguCommented:
There are some differences between 2008 and 2012 RDS, but in essential it's the same procedure. And IMO Folder Redirection is the way to go. For us it is necessary to use roaming RDS profiles, because we use RDS farms (and logons may occur on any of them, so users had a different profile everytime) - and I like to have data apart from settings. So at least the Documents folder points to a location outside of Profile.
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VB ITSSpecialist ConsultantCommented:
I don't think the User Profile Migration Tool can migrate Server 2003 profiles to Server 2012 R2. Even if it could, I wouldn't recommend using it as you may introduce other small issues into a new environment. Folder redirection is the way to go, as pointed out in my previous comment. Method 2 in that article you posted should be able to point you in the right direction.

Do you currently have roaming profiles enabled in your environment? i.e. is the Profile Path: field in the Terminal Services Profile tab for the user account pointing somewhere?
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Seth SimmonsSr. Systems AdministratorCommented:
This question has been classified as abandoned and is closed as part of the Cleanup Program. See the recommendation for more details.
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