the installation story for devs writing windows apps has been dreadful for 3 decades.

vs used to help you build setup.exe, which was always a huge chore to use.

clickonce was launched to replace all this with hosted manifests and auto-updates and modern features like that, and immediately forgotten about because it was so broken. nobody ever used it.

then they brought out WinUI and the windows store, which was so overly sandboxed that it didn't fit most use cases and the permissions system of the store never seemed to line up with the APIs themselves.

then they tried their best to destroy myget by launching winget, which got forgotten about again. now even MS doesnt use their own store.

Anecdotally, yesterday I launched the Windows sandbox to investigate some files and noticed that notepad.exe was not available. A quick research revealed that this is because notepad.exe was replaced by the modern variant with Colipot and shit, which is an AppX package (Windows Store file format). And since the store was ripped out of the sandbox, there's no Notepad in it.

I'm not sure I would say Microsoft forgot about the store. I think Microsoft is like a Dog that has no head, no legs, only tails. And these tails have their own will and don't care about the dog in the slightest.

When I was developing C# winforms applications 15 years ago, I just created a fat signed .exe that was then distributed. Installers and click once stuff was a big turn off for users.

On startup, if not already there, it automagically copied itself to the installation directory, created an autostart directory link and started it from the new location and got killed with a named pipe command. It contained and extracted another .exe that was continuously checking for new versions, downloading them and starting them.

As malwary as it gets but it worked flawlessly!

The windows store nightmare that came after looks dreadful.

Not to mention the need for a code signing certificate, which even in 2026 is a gigantic and expensive hassle to obtain.

You can spend weeks of effort and hundreds of dollars just to ship an installable hello world app these days. The MS store takes care of signing, but there are other trade-offs.

The entire desktop TTHW (time to installable hello world) story is horrible across the board:

- Win: Decent tech foundation for updates made insufferable by code signing requirements.

- Mac: No update story, cobble together a bunch of tools/scripts, notarize releases with Apple (not very onerous), hope you don't ship an update that crashes at launch because you broke your updater too.

- Linux: No consensus on how to package. Bob wants a .deb, Alice wants a snap. Flatpak seems to be winning overall. The best tool to smooth over Win/Mac installer headaches (Conveyor) doesn't support flatpak. Bummer.

Everything my W11 VM has was installed with winget.

clickonce for a brief shining moment was the closest we ever got to being able to deploy an application like a webpage.

I did run into a lot of issues with the store/winrt APIs where there were backdoors that the NTDev team used to work around all the limitations, but they would never publish them.

> vs used to help you build setup.exe, which was always a huge chore to use.

Was it... REALLY though? Everyone knew how to use the setup wizards.