Tidbits on Windows Updates in my lab

I realized I needed to do some upgrades in my lab.  I have Win2K8 R2, Win2K12 R2 and Win2K16.  I like the sound of Project Honolulu (now Admin Center) and it needs Win2K12 and later.  But also I just want to have less version diversity the lab - so Win2K16 wherever I can.  But upgrades have been interesting and thought I would share things I learned.


I normally upgrade in my lab, when in fact I would not do that at a customer but I do it due to MSDN licensing and having a limited number of licenses.
And yes, backups before upgrades is key!

Things I learned

  • I noticed on a bunch of my VMs deployed in the last year or two, that they had Direct IO Path enabled.  Thanks for the guys in the vExpert Slack channel for cluing me in.  At least one of them had performance issues related to this odd issue.
  • On one of my Win2K8 machines I have SQL 2008 so I thought to upgrade it first to SQL 2014.  But I had to update it to SP3 first, I used this article to help with understanding the SQL versions and getting the updates. The SP3 update went good and things still worked after it.  After the 2014 upgrade - which had no error messages, I installed the management tools and tested. I confirmed after the SQL upgrade it worked fine, so I am going to upgrade to Win2K12 to see about if it prompts for a license.  Plus it may make the final Win2K16 upgrade more likely to be successful. However, the Win2K12 upgrade process would download temp files and start, but actually not. Comments on the Internet suggest to go from Win2K8 R2 to Win2K12 and Win2K16.  If I could only get the Win2K12 upgrade to start. I checked the logs and found this article that compares but it helped not at all.  Thanks Ian Noble though.  It is failing on a language thing, but language is not different. Maybe need to try using the language parameters on the CLI?

  • On one of Win2K12 machines I updated, it took a while to upgrade, but then a lot of patches were needed and it took a long time to update. I used this article to help. I did have to add a license, and there were several restarts.  It did not like the VMware Tools SVGA but after a couple of confirms it kept it and continued with no issues. The Veeam Backup & Replication console worked after the upgrade and so did the UniFi Controller. So a successful upgrade and while I thought it would save a license it did not as it needed a Win2K16 license. I have now done this on four Win2K12 machines and the behavior and time is similar. The second one had hMailserver installed and it worked fine after as did things like Autorun and BGInfo. The third one had Veeam Availability Orchestrator and Veeam Backup & Replication and both worked good afterwards. The fourth one had no special apps but the upgrade was smooth and things like BGInfo, Autoruns and Process Explorer worked fine.
  • On a Win2K8 R2 server - when I tried to upgrade it to Win2K12, it said that editions did not match so it had to be a destructive upgrade. It was Standard and I used Standard so that was sort of odd. A restart did not help.  So maybe this Win2K8 VM is not going to get upgraded?
  • After I do each upgrade, I had to power off the VM, and Edit Settings,  VM Options, General Options where I was able to set the OS to the proper version.

Work Outline

Just in case it helps you, or so I can remember it in the future, here is my work outline.

  • Windows Update to current.
  • Backup.
  • Mount ISO.
  • Upgrade
  • Windows Update to current
  • Un-mount ISO
  • Change the OS version in VMware Web Client to the actual version.
  • Test
    • Authentication
    • Major apps like View, Veeam, or SQL
    • Minor apps like Adobe Reader, PowerShell,

Important stuff summary

  • I learned I do not know much about MSDN licensing other then the tactical of consuming them!
  • And yes, I really should deploy new VMs, add the apps to them, and not bother doing upgrades.  And while in the past I was able to save on licenses by doing upgrades I do not any longer.  So maybe time to change my behavior. Think that this will be potentially quicker, and certainly with less odd little issues, and you end up with servers that have less cruft.


  • 4/21/18 - first published.

I will be sure to share as I learn more via this article.

Yes, I have not worked at customer side for a long while.  So maybe I am missing something or did something odd.  Feel free to share your comments and suggestions, I would appreciate it.
=== END ===

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