The Wrong Way to Switch Operating Systems on Your Server

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2021-06-19 04:00:10

After moving my server to Hetzner, I built up a large collection of self-hosted services I use on a daily basis: from fun things like an RSS reader and an IRC bouncer, to critical services like my email. I ran them all with docker-compose from a Debian VPS.

For the last couple months, however, I’ve been meaning to move away from Debian and towards something more minimal and clean. Over this last weekend, I decided to move to Alpine Linux.

In a previous move between two servers, I simply rsynced the relevant files over to the new VPS. Here, where I’m just switching operating systems on a single server, I figured I could make a backup with Tarsnap, and be done within the day.

However, backups are much more complex than simply transferring files from one server to another. My haphazard strategy resulted in three days of stress and frustration as I clambered to restore a self-hosting empire that I myself had reduced to ash.

I began my work on the transition full of optimism, if a bit stressed. I had read through the Tarsnap online documentation a number of times, and was ready to make my first attempt. I loaded my Tarsnap account up with USD$10 and ran:

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