Upgrade Windows 2008R2 RDS to Windows 2012R2RDS

I've read some articles that indicate it's possible to perform a direct upgrade from Windows 2008R2 RDS to Windows 2012R2 RDS.  The articles state that only the gateway and licensing server roles can be upgraded. So, they suggest that you can uninstall the other roles, upgrade the gateway and licensing server and then reinstall the remaining roles that are required.  I have a small client who uses remote desktop extensively. As an accounting firm, they have multiple versions of QuickBooks and other accounting programs installed on their remote desktop server. So, it would be much more efficient and less time-consuming to upgrade the server rather than migrating and having to reinstall all of the applications. In addition, some of the QuickBooks versions are so old that we may not be able to obtain the original software and all of the updates to bring them current.

I'm particularly looking for advice, comments, thoughts from anyone who has actually attempted or done this upgrade. What if any problems were encountered? Did your apps work properly after the upgrade? Do you have any specific advice about steps to do or things to avoid? Other thoughts or recommendations are welcome, except that I don't want to hear from anyone who just wants to say "migrate don't upgrade." I already know that's the recommended path but I have valid reasons for wanting to do a direct upgrade instead in this case if possible.
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Hypercat (Deb)Asked:
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Mohammed KhawajaConnect With a Mentor Manager - Infrastructure:  Information TechnologyCommented:
My two cents for you would be to setup a VMware ESXi on a computer and perform a P2V migration of the server to the ESXi server.  In an isolated environment, you could perform an upgrade to the newer OS and then test your various versions of QuickBook.
CoralonConnect With a Mentor Commented:
I'll be another to beat the bandwagon of 'don't upgrade - migrate or rebuild'..

Having been a Citrix/TS consultant for a lot of years, I've run into many situations where people wanted to upgrade, and I've attempted them all.  Only 1 has actually been truly successful, and that includes these:
NT 3.51 (WinFrame) -> NT 4.0 TSE
NT 4.0 TSE -> Win2k TS
Win2K TS -> Win2k3 TS
Win2K3 TS -> Win2k8 TS (had 1 success here)
Win2K3 TS -> Win2K8R2 TS

All other attempts have had issues ranging from moderate to severe, and other than the 1 case, they all ended up requiring a rebuild.

Now -- that the preaching is done :-)  if you are *still* determined to try it:
1. Get a full bare-metal level type backup -- be 100+% sure you can get back to your working state.
2. Build a new Win2k12 RDS VM, and verify that your old versions of Quickbooks will even run on Win2K12 RDS. -- this is a huge one, especially since you may or may not be able to get the original software.  At minimum, the client should get a very strong recommendation to get their data migrated out of those old versions.. that's just waiting for a disaster to happen..
3. Verify your printing -- this is another huge one that people tend to overlook, especially with older software.  Many pieces of older software can't necessarily handle newer drivers/newer print mechanics.
4. Verify your profile backup information -- doing an OS upgrade will frequently change some software registry keys, and make some of them simply invalid from the upgrade.. (again, depending on the software, and what it is expecting).  Find out if you have the option to delete profiles so that you can have them start cleanly.
5. Again -- old software.. verify that it is not using HKLM for any user-level type settings.. (this has been a thorn in my side many times with software from the NT days..
6. Since you are dealing with older software, verify if anything was configured using the usrlogon.cmd mechanics (see my article - https://www.experts-exchange.com/articles/9235/How-USRLOGON-CMD-processing-works.html).  I have seen a number of occasions where people thought they knew what they were doing, but installed script code into usrlogon.cmd which was wiped out by the upgrade process, when they *should* have put it in the correct directories and called if from usrlogn1.cmd or usrlogn2.cmd (and be sure you know the difference between the 2 :-)
7. Lastly.. verify that the software licensing will survive the upgrade.. Intuit has always been very bad about forcing all of their software to be deeply tied to the OS & hardware of the system it was installed on (from a licensing perspective), and if something major changes, it may simply decide it's unlicensed.

Good luck!

Hypercat (Deb)Author Commented:
Thanks for your advice, Coralon.  I'll take it under consideration. I want to reiterate and expand on the QuickBooks issues:  this is not my client's choice.  These versions of QuickBooks are kept because my client has clients that are using those versions and he has to be able to open their QuickBooks databases in order to support his clients.  So, as his computer consultant, I don't really have any input into the situation other than to say to him, "you really should get your clients to upgrade to a new version of QuickBooks!" That said, I agree that we need to confirm as much as possible that these versions will run on Windows 2012.
Hypercat (Deb)Author Commented:
It's already a VM, but now that I think about it, I could clone it and use that as a test. If it works, then I'm done.  If it doesn't then I have to start over.  That's actually a great idea - now why didn't I think of that?!!
Hypercat (Deb)Author Commented:
If we decide to go ahead with this project at all, we'll use the suggestion of doing a test upgrade to see if it will work.  If the client won't pay for that (which I'm guessing at this point they won't), then we are going to scrap the project entirely and leave the RDS server at Windows 2008 R2 for now.
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