These are some notes on my experience of upgrading Debian from Jessie to Strech.

First I skimmed through the release notes, but I couldn't find anything there to cause alarm so I didn't expect any major trouble during the upgrade. Before doing anything else, I made backups of /home, /etc and /var, just to be on the safe side.

The next step was to edit /etc/apt/sources.list and change every instance of jessie to strech and then we get to the scary stuff:

# apt-get update
# apt-get upgrade
# apt-get dist-upgrade

I use apt-transport-tor so the downloads took forever, not that I was in a rush but a small annoyance nevertheless. A small note to self; if I were to do this again in the future, disable apt-transport-tor during upgrade!

The apt-get upgrade went smoothly but sometime during apt-get dist-upgrade, after all of the downloads finished, my laptop decided it was an appropriate time to overheat and shut itself off. Very inconvenient timing. It's a weird, sometimes it doesn't understand that overheating and that it might be a good idea to turn the fan on.

I let the machine cool down for a bit and booted it up and tried to just run apt-get dist-upgrade again but got lots of errors, as expected. Mostly dependency stuff. After several dpkg --configure -a, apt-get -f install and some apt-get --reinstall install package-name I managed to get to the point where I simply could run apt-get dist-upgrade without getting any errors. That was pretty much it.

Now some changes I've noticed so far:

• offlineimap now requires an explicit fingerprint of the IMAP servers SSL certificate in .offlineimaprc. The output is also slightly different.

• I got a weird error from mutt when starting it; press key to continue. I didn't have this problem prior to the system upgrade and it turned out the actual error message was suppressed due to my extremely clever alias alias mutt='torify mutt 2>/dev/null'. It's not easy to track down what's going wrong when you send all the useful information to /dev/null. I had set a nonsensical charset variable in my muttrc.

• When starting mutt I also got this error GPGME: CMS protocol not available on startup error which I couldn't find a reasonable solution to so I caved in and reinstalled gnupg2, gpgsm, gnupg-agent libgpgmepp-dev, and libgpgme11.

• Another thing I noticed was that mutt, or perhaps more correctly gnupg-agent now remembers my gpg-passphrase between mutt sessions for some time span. I don't like this.

• My monitor now gets a nice 1920x1080 resolution out of the box, everything is small!

• There was some trouble with tex-live but I was lazy and tired so I just purged and reinstalled it.

• Some packages just disappeared from my system into oblivion e.g. mpv and network-manager-gnome. Wtf?

• My Swedish dictionary for aspell also disappeared.

• Good news! Debian Stretch ships with the free mathematical software SageMath. I've only played around with it a little before and If I remember correctly I had to compile it myself back then. I'm currently working my way through their excellent tutorial, fun stuff!

• SSH sandboxing.

• pulseaudio default sink is now 0 instead of 1. Had to update some keybindings in i3.

• My mpd + pulseaudio setup broke. Spent some time trying to fix it but I wanted to listen to my music so I purged, reinstalled and reconfigured everything according to this.

• My instance of nikola (the program I use to generate this blog) disappeared from my system even though I had installed it via pip. Hmmm?

• keepassx now uses a new database format. Luckily it was very easy to import my old database and convert it to the new format.

Otherwise everything is pretty much the same in userland. I'm not a poweruser and I boot directly into tty1 and then startx into i3 where everything was the same.

I have a feeling that I might stumble upon more problems from this upgrade later on.