Windows 10 upgrade troubleshooting

Windows 10 has been much talked about over the past week and a bit. While I took the opportunity to do a clean rebuild on a new SSD for my main desktop, I also had a laptop which I’d planned to try the upgrade process with. The only issue was that the “Get Windows 10!” task tray icon simply wasn’t appearing.

There’s a lot of blog posts detailing tips and tricks to force the update process to work, and over the course of a few days it felt like I’d tried them all. From clearning the SoftwareDistribution\Download folder and running wuauclt.exe /updatenow through to various shenanigans with GWX.exe and scheduled tasks, I’d jumped through all the hoops, all with no luck. I also tried the media creation tool, and received the incredibly useful “Something happened” message.

None of these processes provided any feedback at all. I had all Windows updates installed, and it was a genuine version of Windows that should have been eligible for an upgrade. Something was clearly wrong here.

It was this post that led me to identify what it was. The post is a pretty comprehensive list of all the various troubleshooting steps, combined into a single reference point. Nothing listed there worked for me, however one of the updates towards the end of the post mentions that Microsoft has released a troubleshooting tool.

I grabbed the troubleshooting tool, and ran it. The first run seemed to confuse it, and it claimed there was an issue with Windows Updates which it fixed (thanks!), only to then display a message telling me my version wasn’t eligible for an upgrade. However I ran it again, and it informed me that machines that are joined to a domain aren’t able to be upgraded. I run a Server Essentials 2012 box at home, so laptop was joined to a domain (which is of course optional) – I left the domain, and lo and behold the icon appeared, and the Windows 10 upgrade ran flawlessly.

(Incidentally, if you’re also a Server Essentials user, then you’ll want to download the latest version of the connector here)

That was a lot of work to get the icon to appear, and I came very close to giving up and nuking the build from orbit a couple of times, but I really wanted to test the upgrade experience. While it’s apparent that there’s quite a few things that can cause issues with the upgrade experience, if you’re having trouble then it’s likely that working through all the links here will see you right.

Download Troubleshooting tool for Get Windows 10 app

Windows Server Essentials Connector for Windows Server 2012 R2 (Updated July 29th 2015)

Posted on Monday, August 10, 2015 10:49 AM |

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