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Migrate Windows Server 2008 Terminal Services Users/Settings/Programs to 2008 R2 Server


I am working on replacing a 2008 Terminal Services Server. There are a LOT of programs/applications (and associated settings) along with users that use those programs.

Is there a simple way to migrate all that data to the new server without doing it by hand? Also, I need to migrate the CALs as well.

If there's any downtime involved in any steps, please let me know.
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The CALS reside within the terminal services License server. usually it the licensing server/service is one of the DOMAIN controllers.

Are the terminal users using ROAMING profiles?
If not do the terminal users use Have Redirected folders?? If it is not present, this is the least intrusive process and should be considered/done first. The login when the data is being copied/moved will take the longest.  After the copy/move is complete subsequent logins will be faster.  Make sure to evaluate whether you want to configure the redirect GPO to revert copy/move the data back into the profile when the GPO no longer applies to the user.
Do the terminal based users use Outlook to retrieve and locally store their email?
Depending on the version and your settings, this could be an issue since some version of outlook stored the .pst file in the %userprofile%\ local settings local that are not copied with roaming profile and are not redirected. The PST files have to be migrated manually by the user or by a script and could pose a headache.

You can save time and resources by at least setting up a GPO that will redirect the users' folder my documents/documents, Appdata/Application Data, Desktop, start menu.
After two logins the data in these folders will copied out to a share (a domain share (DFS) is preferable even if you have a single server that will hold the data. This provides  you the flexibility of using DFS-R when an additional File Server or transitioning to a new fileserver is needed.  using Domain based share and DFS-R, you can replicate the data from the current server to the new server. You can then transition the DFS share targeting from the old server to the new server without hiccups. Without issues that one runs into when transitioning from oneserver to secondserver where many things have to be changed or using/setting up the new server to use the name of the old with no fall back position.)

The issue with installing software is unavoidable. But it depends on whether you want all users to have access to all application or whether you designate/allocate which user/group of users have access to which application.  Look into using Application publishing.
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Installing software I can deal with. There's not that much on there and I don't mind doing that individually. The problem is really going to be setting up the user's profiles. They are not roaming profiles unfortunately. And I don't think I can convert them to be. The users are used to their PC profiles and their Terminal Server profiles being different. So that being said, how can I get the profiles from one server to another easily? I just dread logging in to each one individually and setting up their Outlook, Internet Explorer preferences, etc.

For email, yes it uses Outlook. The old Terminal Server has Office 2003 installed. I'm planning to upgrade that to 2010. Would I be wise to install 2003 for the migration and then do an upgrade?
Roaming means the users can have separate workstation and terminal server roaming profiles.
Within the profile tab for, \\domaindfs\userprofile\%username%
Within the terminal tab,\\domaindfs\terminalserverprofile\%username%
You can also use GPO for defining roaming profile storage location

Within AD look at the terminal connection configuration tab.
You possibly could migrate the profiles if absolutely necessary using the migration wizard.
How would I go about migrating via the wizard? I didn't know that existed.
Since users access both workstations and terminal services, you already have folder redirection setup so that the users can access their documents without regard to which platform they are working on.
Can the user access their emails from both platforms or you have usually users accessing using a single method and emails are web based on the terminal server via OWA.
Outlook access, they leave the mail on the server (exchange/IMAP) email access mode?

USMT is the tool to transition office data with user profile migration.

One option you might try with a test account is to convert a local profile into a roaming one.
I.e. create a share for terminal server profiles.
Modify a test user AD record for terminal server access to point to the share\%username%
On first logon after the change since there is no existing data in the remote location the user will login with the data loaded from the "local" profile. Upon logoff, the data from the local will be copied to the share. Once you confirm this works, this is the best and automated way. The only issue is that a user has to login at least once as a new session versus resuming a prior session.
So once you confirm that it works, the sooner you implement the transition,

There are two options. One deals with backup/restore.
The other deals with live, I.e. you run the migration wizard on the old system, you then run the migration wizard on the new system directing it to the old server for the data, you then select the user data you want transferred in.
The users should be logged off when you run this process.
I'm having a hard time following but it sounds like if I convert them to roaming TS profiles, we'd be fine? I'd essentially have to convert them, log every one of them in on the old server, then log off the old server, log off the old server, log on the new server, and the stuff should be there?

As far as email- most are exchange with maybe one or two exceptions. They aren't all local exchange (some users we host files for use their own exchange service) but they should mostly be exchange of some kind. Does that help?
You can test the conversion from local to roaming profile.  There is no need for you to do anything in this scenario outside the AD user alteration. There is also no need to login to the new once you confirm that the profile on the old system went from local to roaming.

With outlook you have to be sure that they do not store their email in the local path of the profile as well as their contacts. The local settings portion of the profile DOES NOT get copied in a roaming profile setup. The contacts in outlook might also be stored within the same location and could be lost.
Presumably, you have user data backups just in case.

The loss of outlook data is the highest concern. 2003 has issues with accessing the .pst file over the network.

What is the transition timeframe you are working with?
Very short. Like within a few days. Ideally I'd like to complete today or this weekend.
Do you have folder redirection enabled? <<<<<<<<<<<<<<<<<answer please!!!!!!

The local profiles, do you have administrative access into them?
Using robocopy /sec
Make sure all users are logged off the terminal server prior to running robocopy.

You could look into using DFS-R to replicate the data from the current to the new.

Make sure to use the current server as the source of the data that will replicate.
Make sure to have a backup as well.
Seeing as I don't know what folder redirection is, I do not believe I have it enabled.

I do have access to the user profiles. I have all of their usernames and passwords at a minimum but I'm a Domain Admin so my login opens up whatever I want.
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We do have Documents mapped to a U:\ directory if that's what you mean. Other than that there's nothing special.
To minimize the size of the profile folder and speed up the login process as well as maintain application settings across platforms, I would suggest the addition of the other four items to the redirected list including favorites.  This provides several safeguards, i.e. back is only needed on the server of user data versus having to look at backing up individual workstations.

robocopy is a good way to transfer the data.
Using user file backup c:\users
then restoring the .bak file excluding the Administrator/ive accounts should work.
You can test after the restore by logging in on the new server as one of the users to see whether the copied profile loads or not.
I'm still fuzzy on exactly what it is I need to do. So I'm just going to RoboCopy the data from old server to new and see what happens? No roaming profile or yes roaming profile?
Currently, you do not have roaming profile.  The limited timeframe for the transition as well as the (outlook) and partial folder redirection, makes it difficult to transition from local to roaming profiles in time to complete the task this weekend.
That's fine. If it is going to slow us down copying the local data over is fine with me. Just as long as it works. I'll give it a shot and let you know how it turns out.
Thanks for the help man