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As @vsl-iil mentioned in mandiant/flare-vm#577, at the moment our installer tries to reinstall failed packages when a reboot occurs. This is because how the installer is implemented and it is annoying for packages that are broken. Ideally, we want to re-try failed packages installation once after installing all packages (#1219), but not on every reboot. This makes that packages that are installed earlier are re-tried many more times. I am not sure if there is a way to avoid packages to get reinstalled, @mandiant/vms any ideas?