Upgrade Rails 101: The Roadmap to Smooth Upgrades

Upgrade Rails 101: The Roadmap to Smooth Upgrades

This year's RailsConf was a special conference for me. It was my third time attending and my first time speaking at the conference. I conducted a 2-hour workshop for anyone interested in upgrading their Rails application: Upgrade Rails 101: The Roadmap to Smooth Upgrades

Here are a few lessons learned from running such an ambitious workshop.


I believe the scope was way too ambitious. I pitched the workshop as an opportunity to bring any Rails application and leave with a roadmap to upgrade to the next version of Rails. As if that was not enough, I told attendees that they could use a sample, open source application to practice our steps to upgrade: https://github.com/alphagov/e-petitions

I should have used only the sample application. As the workshop went on, I found myself addressing issues regarding random Rails applications and the sample application.

All Environments Are Different

When starting the set of exercises, there was a slowdown addressing environment issues. There is always something slightly off about someone's environment that throws a wrench in the works.

This could have been much simpler providing a Dockerfile and requiring attendees to have Docker installed. That way, the setup would have been something like "just run docker-compose up" and done.

More Details

When describing the steps to create the Rails upgrade roadmap, I should have provided even more detail for every step. For people that were stuck in a step, I could have had branches on my sample Git repository. For each step, I could have had a checklist to make sure that the attendees got to a stage that would not stop them moving forward.


I'm very happy with the feedback I received after the workshop. It was a great experience and I plan to keep conducting this workshop in other conferences. There is certainly room for improvement and I'm sure the next iteration will be even better than the first one.

I will be conducting a new instance of the workshop in the next Southeast Ruby. I hope attendees will learn from our experience and avoid typical mistakes.


Here are the slides from my workshop:

Unfortunately this time the workshops were not recorded, so I won't be able to share a video with my presentation. You can find the companion page for my workshop over here: https://fastruby.io/upgrade.

Finally, if you are interested in upgrading from Rails 2.3 all the way to Rails 5.2 you can read all of our articles from our Rails Upgrades series.

This workshop is a by-product of our productized service: The Roadmap. I wouldn't have been able to conduct it without the support by the team at OmbuLabs. Thank you all!

If you're not on Rails 6.0 yet, we can help! Download our free eBook: The Complete Guide to Upgrade Rails.

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