[LegibleCrimson]

Don't package managers solve this? Maybe I'm in a bubble, but I was under the impression that good package managers existed for all major desktop OSes. Surely Windows and MacOS aren't still in a situation where apps are expected to regularly check for updates and upgrade themselves, right?

[thereticent]

For Windows, false, unless you install it through the "Microsoft Store"

[hammyhavoc]

Chocolatey exists and supports Calibre.