Earlier quoted context omitted.
autoremove removes packages that are no longer used and should not affect anything. However, if you have messed with your system (eg manually copied some software or edited a configuration you should not have touched) then autoremove may remove things the system now needs to boot. How do I know this? Because I once did exactly that (to be fair, apt-get told me this could happen and asked for a second confirmation)
I know what it should do, and I use it regularly. That one time, it triggered or caused Xenial to stop working correctly.
Kind if off-topic, but I have to ask. Why do you use autoremove regularly? The amount of storage that is wasted it negligible so I barely bother with it, even inside vms and containers which often have tiny filesystems.