AutoIt can get really fun when dealing with non-interactive sessions that WinRM is run on. The behaviour around console windows in session 0 is not the same as a normal interactive session you get when running it manually. If AutoIt is waiting for specific console state or is trying to click a button in the wrong area it won't work as expected. So effectively the problem isn't Chocolatey, Ansible, or win_chocolatey, it's using AutoIt in a non-interactive session that is a byproduct of WinRM. I don't know enough about AutoIt to give you tips on your scripts but ultimately you want to try and have some sort of timeout that will fail if it exceeds a certain time. This won't help with getting it working but it will at least tell people what the issue may be instead of just hanging.
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