Breaking Servers and Learning By Trial

I mentioned in the past that I run my own mastodon instance. You can find it at, where I’m ostensibly creating a community for LGBTQIA+ folks who are interested in technology.

I chose to wait until this morning to update Mastodon to v2.4.0 on the server that I host this instance at, thinking that I would be able to complete it in a half hour at most based on some of the last few updates.

What followed was a multi-hour ordeal; something that took up far more of my non-work time than I would care to admit. At the end of the day it turns out that I had missed running one command early on in the upgrade process that led to a cascade of failures later on.

My general ineptitude with Ruby, bundlers, and Docker were my downfall, in which I wasn’t sure of the commands that I should run to diagnose issues, and I wasn’t sure where the errors that I received should leave me, beyond the suggestions in the terminal that were trying to save me from myself.

With a break, far more patience (or foolhardiness) than I expected to have, and plenty of help from Chris Wiegman, I ended up finding the source of my woes and updated the server and software properly.

Recounting this is partly an excuse for writing something so short so late, but it’s also a reminder of something that I said earlier in the month: despite the additional tools, libraries, tutorials, and packages, the difficulty level of becoming a web developer is Growing.

Photo by Tim Gouw on Unsplash

I can’t rightly assume what things that I do every day should be a standard for building on the web, considering how trivial some of the problems that I grapple with must seem to others. I’m glad to always have something new to learn, but at times it can be quite exhausting.

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