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Trying to troubleshoot failing Insider upgrade


A few days ago I wrote about my efforts in upgrading a Windows Insider build from 18898 to 18908 (full story). Despite several successful upgrades to new Insider builds beforehand, that upgrade failed every time. I tried everything I could think of, and everything I know, to fix this, but failed miserably on all attempts. Finally, I gave up and created a new 18908 deployment image on a Hyper-V virtual machine, and deployed it using an MDT LiteTouch installation. Everything turned out OK.

Yesterday, the Windows Insider team released build 18912. Thankfully, my freshly installed 18908 had no issues in upgrading. When upgraded, I made a full Macrium Reflect system image, and decided to play around a bit. I restored an earlier 18898 image, and re-tried all of the different upgrade scenarios trying to get to 18908. Thus, it was the same upgrade path I had tried and failed last week. I had to use an ISO image, because Windows Update would have offered build 18912.

Once again, I garnered the same results: the upgrade failed, no matter what tricks and workarounds I tried. OK, my next step was to try to upgrade that 18898 to 18912 using Windows Update. Everything went smoothly, and that skip-a-build upgrade completed without issues.

It’s a long story, so here’s the short version: After ten or so build upgrades without a clean install, I had no issues. Then, for the 18898 to 18908 upgrade, I hit a wall. Nothing worked, and it wouldn’t upgrade. However, skipping 18908 and upgrading to 18912: here again, no issues presented. Thus, I must conclude that something in build 18908 made it impossible for me to upgrade. At this point, I have not the faintest clue what that might have been.

This, of course, comes with the territory. As a Windows Insider, sometimes you really hit the wall and are forced to start over from scratch. I like it: troubleshooting is as far as I know, the best part of computing. OK, this time my troubleshooting didn’t help, I am quite puzzled and confused, not knowing what it was in that one build that made my upgrade impossible. But, I will continue troubleshooting. Because I have a full image of my system made before the first attempt to upgrade 18898 to 18908, I can mount it as a virtual machine in Hyper-V using Macrium viBoot, and continue testing. Most probably I will never find out the reason for that one specific upgrade to fail, but it will be fun to try!

Kari

 

Author: Kari Finn

A former Windows Insider MVP, Kari started in computing in the mid 80’s writing code for VAX / VMS systems. Since then, he’s worked in a variety of IT positions. He specializes in Windows image capture, customization, repair and deployment as well as Hyper-V virtualization. Kari is a proud Team Member at number #1 Windows site TenForums.com.

2 Responses “Trying to troubleshoot failing Insider upgrade”

  1. June 6, 2019 at 19:42

    It’s a “Feature” in the build that doesn’t like something on your system (i.e. driver, firmware, bios, etc.), which was rectified or removed from 18908 and not indicated in the “Fixes and Foibles” section that MS so eloquently puts together after each and every build. But you are most likely correct, you’ll never find it, and they will never divulge what it was either. Just my 2cents worth

    • June 7, 2019 at 22:26

      It’s the fact that I am not able to find any reason that keeps me trying. 10+ upgrades, all worked, then comes one upgrade that breaks that. Skipping that one build, upgrading to next one works again.

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