I recently realized that my web server was still on Debian Buster, 2 whole major versions behind the latest Debian version. Normally this kind of thing wouldn’t matter to me except that my matrix-synapse server was unable to federate with matrix synapse servers running newer versions. I normally run rolling release distributions on my local machines (I use Void btw) and it had been a long time since I tried this kind of upgrade. I went in hopeful that it would be straightforward.