Gfilui

My Ubuntu version is 16.04 LTS. I have been getting "Low Disk Space" message. An example of the message I get: "The volume "boot" has only 3.1 MB disk space remaining"

Things I have tried when I get such a message:
1) Deleted old kernels using sudo apt-get purge linux-image--generic
2) Cleaned up various directories
3) sudo apt-get autoremove

None of these have helped. In fact, running 1), 3) made my system fail to boot. Every time my system fails to boot, I re-install an old working image of my system. After a few weeks, I once again get the Low disk space error.

What can I do to prevent /boot running into low disk space?

I'd appreciate your help.

P.S: I am not a sys admin so I'd appreciate more context in your answers. Thank you!

Edit 1:
I had previously tried the solutions provided in the suggested links. Running 'sudo apt-get purge' made my system failed to boot.

Edit 2:
I am running sudo apt-get autoremove preemptively. That seems to keep the problem under control. Are there any other ways to get rid of the boot low disk space issue instead of running sudo apt-get autoremove preemptively every few days/weeks?

When running sudo apt update && sudo apt upgrade the system will tell you if there are automatic installed package that can be removed by running sudo apt autoremove .. when that happens, run the autoremove, this will , among other thing, remove old kernels from /boot