It’s been a year since I moved my company’s infrastructure away from AWS. Being in a small team that was unfamiliar with AWS, it was the right move. Having used Fly.io for side projects before, I went with them as our new host. While not perfect, the experience has been overall a great success.

The main motivation was how simple and hands-off Fly is, especially when compared with its polar opposite, AWS. There was quite a lot of infra cost savings as well. Here’s a quick summary of my overall experience and feeling on them.

TLDR We launched Podlettr - go check it out!

For nearly two years, me and my good friend Sérgio Fontes, an accomplished product designer, have been working on Podlettr - a great way to quickly catch up with your favourite podcasts. As the name implies, Podlettr is a letter from your podcasts. Reading is faster than listening, and with some AI magic, we convert hours worth of podcasts into beautiful, easy-to-read weekly newsletters.

We both have demanding full-time jobs and family duties, so we had to be pragmatic with the frameworks and architecture choices we made. Rails was my obvious framework of choice. Within weeks of the initial idea, we had a working prototype.

Ideally, deploys should be small, concise, easily revertible, fast and with a small or nil footprint on the database. However, no matter how awesome you are, sometimes that is just unattainable and you end up needing to deploy something that is just the opposite: big, messy, hard to revert, painfully slow and rubbing the DB the wrong way. If the deploy messes with a mission-critical part of your software, all the worse for you.

But there are actually many ways you can make those situations even worse. Here are a few bullet points you can follow to guarantee a nightmarish deploy complete with nasty side-effects that will haunt you and your coworkers for days to come.

Try searching for “free dynamic dns https”, “free domain with SSL” or anything similar. There won’t be a lot of meaningful results. Sure, some of the results are pretty close, like this guide on how to get free SSL certification from Cloudflare, or this one on setting up a free dynamic hostname with SSL, but they all assume you already own a domain. If you’re looking for a completely free domain that you can use for your personal web server that also has verified SSL, there are very few results.

But why was I even looking for this?

I’m working on a side project. It has a web server that communicates with a static web page hosted on Github Pages. There are a lot of ways of setting that up; in my particular case, I have a local (as in in my house) HTTP web server accepting traffic on a non-standard port (port 80 is blocked by my ISP for commercial reasons – this detail is of paramount importance, but more on that later). It is accessible through my external IP (which is dynamic), which can be mapped to a dynamic DNS domain.

I wanted to run a simple API on the web server and access it through static pages (like this blog) hosted on Github Pages (which has a verified SSL certificate). I asked the Internet if it is possible to call from a SSL-verified page (in JavaScript) a different server that does not have a verified SSL certificate (that is, my aforementioned webapp running in my home server). It isn’t, so the conclusion was that I needed somehow to get a verified SSL certificate for my dynamic DNS domain.

Having no idea whether this was possible, I started to research.