Had the same for 2 Debian boxes when a new X was introduced (it was the upgrade from Debian 7 to 8). You see, they told me that because I use different repositories I was "unsupported". So I did try the suggestions to upgrade to unstable (which I had experience being in because at the time I bought my system, I required that to get network working, but every apt-get update is a surprise, unless you read the logs carefully before saying "Y"...). So after not getting gdm/kdm working, and bypassing that with other window managers, I finally reinstalled because I could not get gnome nor kde to work (plus I had zapped so many software, I could not do work anymore; but briefly my desktop looked like the Padora ). Reinstalled with the Debian 8 CD... and guess what? They still did not adjust the sizes of the FS, so they are all wrong. So I ended up (tried it twice, so it IS a Debian bug) with a / of 315MB (196M available). So each time I get a kernel upgrade... I have to move the /lib/modules/ to my home, symlink them, upgrade, then put it back, because they put the temporal next to it, and having more than 2 does not fit...until some update broke my system.
So how do I have 196MB free on / ? that is right.. I permanently moved the system to the /home FS and keep it together with ducktape (because if I have a FS corruption on home, I can not boot).
107M /home/system/lib/modules/3.2.0-4-amd64
163M /home/system/lib/modules/3.16.0-4-amd64
But wait.. /root is also on / so what happens when I start graphically as root? that's right... .kde .firefox and so on... before you know it /root is bloated.
Why am I not reinstalling my system ANOTHER time? Because LUKS takes almost 4 days to format my 2TB hdd.
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Wait... YOU don't carry a Linux disk around at all times? (Rescatux, a life Knoppix or OpenELEC or BERT?) Then what do you carry? Swiss knife? Screwdriver set? Portable Fire (lighter)? Medikit (band-aid)? Chewing gum (for when you forgot to brush your teeth)? safety needle? laserpointer? An elastic? a napkin? not even a Zombie Apocalypse Survival Kit?Why do you carry a Linux disc around?