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Comment by NickGerleman | Hacker News Reader

I've definitely had issues doing an upgrade on a real Ubuntu installation. Years ago I needed to update a more or less clean install of Ubuntu Desktop. It managed to completely break Gnome somehow (This was before Unity). I'm guessing things are better now and that the server distribution is better for this but I could see complications happening.

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I used Ubuntu Server LTS a couple of times.

The 14.04 version which is supported until 2019 still has the bug that it won't clear out old kernels after upgrading them. So if you don't look into your /boot partition now and then it fills up and breaks your installation.

Can you link to a bug report? dist-upgrade (as opposed to upgrade) should remove the old packages;that's its whole point...

Xe could hyperlink you to Dustin Kirkland's call for feedback here on Hacker News only a short while ago, where this subject came up several times. This is a well-known Ubuntu problem, and M. Kirkland xyrself said that taking purge-old-kernels out of the byobu package and putting it somewhere more obvious was a good idea.

* https://news.ycombinator.com/item?id=14002821

Of course, this is an Ubuntu upgrade problem relating to Linux. It is specifically about kernel image files. So it has very little application to the Windows NT Linux Subsystem, which as we know uses the Windows NT kernel.

I'm sure you know but apt-get autoremove

After a major change of desktop like a switch from gnome 2 to unity or gnome 3, it is not surprising that users may need to refresh their configuration files. I am doing dist-upgrade since 2009. They were all smooth except the upgrade to 16.04 (lost of network and a couple of small issues still not fixed).

After 15 years with Ubuntu, I've only ever seen problems when people switched default Ubuntu packages with their own (back in the day it was often beryl, compiz or drivers).

I've had this problem many times in the past too. Including subsequent problems with dpkg after the upgrade to 16.04

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