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Upgrade Server OS from 2008 R2 Ent. to 2012 R2 DataC.

I'm attempting to upgrade my backup server from Windows Server 2008 R2 Enterprise to Windows 2012 R2 Datacenter.  I've attempted the upgrade twice so far and have, most likely, corrupted the process myself thru impatience!  The process runs it's course and everything appears to be working but it's running for over 2 days and, after 1 full day of seeing "Preparing to Start" (or something to that effect), I get impatient and force a reboot which ends up telling me that the "upgrade failed"....Has anyone performed this upgrade successfully?  If so, can you let me know if it typically takes more than 2 days and whether or not I should try it again with a little more patience.   Thanks!
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SILVER EXPERT
Distinguished Expert 2019

Commented:
are you doing an in-place upgrade?

Much depends on what it is doing. Often in such a case, decide how long you are willing to wait.
Depending on the amount of data on your windows 2008, an option is to virtualize this system. install 2012 from scratch with hyper-v and attach a copy of the  win2k8 's VHD/VHDx and try the process in the VM while allowing it to take as long as it needs.
dsik2vhd from Sysinternal's MS portal.
another clone it using vmware's converter and use the free ESX host to set it up for test....


You know what you may find if you let the process go which I've learned some time ago, is that it might have been an additional 20 minutes in the "Preparing to start"
This is a backup server to what and for what? If extended outage is unacceptable reconsider how to achieve what you need.

Does the hardware support win2k12?
Jim KlocksinOwner, Data Architects

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Commented:
First, Yes, I'm doing an in-place upgrade and I am willing to wait for as long as it takes (I've actually started the process again...).  I've never worked with virtualization (at some point in the near future I do want to learn more about setting up a virtual server) and, at this point, I just want to see if I can get this to work.  Based on your comments, along with my past attempts, this time I'm just going to let it run for a week if that's what it takes....Thanks!
SILVER EXPERT
Distinguished Expert 2019

Commented:
Upgrade often depends on what the system being upgraded did as the in-place has to add related roles, features........

Good luck.
Jim KlocksinOwner, Data Architects

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Commented:
The in-place system ran remote desktop applications, had over 700 users in Active Directory, was a domain controller, DNS server, and database server (SQL Server 2008 R2).  So I had a lot of stuff going on but it was limited in scope to providing RDP apps and nothing else other than what I already mentioned.  Not sure if all the AD users is slowing down the upgrade but it's been running since my last comment and is now in the "Getting Ready" mode with the "circle of dots" going round and round.  If I'm lucky, it may end sometime over this coming weekend, but, if not, I'm just going to let it keep going since it's intended use was as a backup to the live server which is set up the same and providing the Remote Apps for my client.  Thanks, I'm keeping my fingers crossed!
Owner, Data Architects
Commented:
All it took was a little more patience.  After about 4 days, the server was upgraded to 2012 R2 server successfully.  I attempted to upgrade to 2016 server after that and that ran for about 2 days until I had an electricity problem which caused the server to shut down.  At that point, I just decided to restore my original 2008 R2 server.  I will probably attempt these upgrades again at some point in the future when I have more time to "play"!