Chocolatey

Raised as a usability problem by 7 people on Hacker News over 9 years (2016–2024), in 7 threads.

People raised many different problems with Chocolatey, but no single problem has yet been raised by 3 people in 3 different months and threads.

Unreviewed issues were grouped by machine: Claude Haiku labelled each comment as a usability complaint, named what it's about and summed up the problem in a line, and a small model grouped similar problems. Nobody has checked them by hand. Expect mistakes.

The newest 7 complaints

Setting a default install directory required a paid tier, forcing explicit paths in every command2024-09-11
Commands leave apps in inconsistent state, blocking upgrade, uninstall, or reinstall without manual fixes2022-04-20
Shows incorrect install and version info and fails to upgrade properly2022-03-31
Multiple duplicate packages per app, with no reliable way to tell which is main2020-05-19
Python installed under WSL cannot be used alongside Windows Python, unlike Homebrew on macOS2017-11-12
Searching for grep returns a dozen confusing, unclear alternatives instead of the tool needed2016-03-30
Install arguments differ per package and are poorly documented, so users must guess2016-03-15