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I have 50+ Windows Servers with 2008 R2 OS, they have diverse roles installed, like some are DCs with DNS, DHCP, etc. Some are File Servers, Print Servers, WTS Servers, IIS and so on. They are all VmWare VMs. We are planning to upgrade them to 2012 R2. The question is about the best and not-so-painful way to do this. Some guys suggested me to create secondary VMs and install 2012 R2 on it, migrate the roles and then turn off the old ones. I have even tested in lab the media (in-place) upgrade with DC roles and all the stuff installed and working. It upgraded surprisingly quite easily and fast, and everything came back normally. But I don't know if this is the best practice. Do you guys have any suggestion?

Thanks in advice.

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    I don't think there's a "best practice" for that. If you can, keep it clean and "redo" them. If you can't, do an in-place update – MichelZ Jul 16 '14 at 12:12
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    Seconding full reinstalls. Have had some success with in-place upgrades before, but have also had them cause plenty of headaches. – jski Jul 16 '14 at 13:41
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    I'm on the same side. In-place upgrades might work, but there will always be at least one system that has some 3rd party software running on it which doesn't survive the upgrade or blocks it in the first place. I would go for fresh installations and transferring the roles to the new systems if necessary. – desasteralex Jul 16 '14 at 19:00
  • Just went through this process myself. Fresh install and migrate roles. Most roles are designed to do this and most Microsoft Technet articles walkthrough this process. – Byron C. Jul 17 '14 at 15:42
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I have had great success with Inline Upgrades and this is going to be the norm moving forward. Legacy administrators will be stuck in legacy ways administrating systems. Microsoft has overhauled its inline process to ease the burdens of past experiences.

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