Struggling with Winget: Installation and Update Issues

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Asked By TechieWanderer42 On

I'm trying to use Winget to install and update several applications that aren't part of our usual management solutions, but I'm running into a lot of issues. I'm executing Winget under the system account through our RMM.

My first attempt was to update the Draytek Smart VPN client for a user. I hit a snag with an error saying it was installed through a different method, so I uninstalled it using Winget, then reinstalled it. However, when I try to launch it from the Start Menu, it prompts for the MSI installer location. Interestingly, I can open it directly from Program Files just fine. I also tried a clean install, and the same problem occurred.

Next, I randomly installed SumatraPDF, and while Winget confirmed it was installed, I can't find it listed in 'Add/Remove Programs' or in the Program Files—it's like it doesn't exist. When I try to run the install command again, Winget tells me it's already installed.

I then attempted to install Greenshot, and it just gets stuck on 'Starting package install' without completing.

Is this typical for Winget, or am I missing something here?

2 Answers

Answered By CuriousAdmin88 On

I haven't had problems installing normal applications and developer tools with Winget. Have you looked into using a Winget wrapper? There's a great one called Winget-Install that might help you with managing updates better. Here's the link: https://github.com/Romanitho/Winget-Install.

TechieWanderer42 -

Thanks for the suggestion! I tried it with the Draytek VPN client, but sadly ran into the same installer issue. Still, it's a nice tool!

Answered By InstallNinja23 On

I've used Winget a lot, but I haven't tried those specific apps. Have you tried running `winget upgrade winget` first? It might help clear up some issues before attempting those installations again.
Also, I know MS Teams can be a pain with Winget, so that might be a related issue.

AppGuru99 -

Did you check to see if the issues persist when not running under a local system account? That could be a factor!

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