Upgrade Rails 101: The Roadmap to Smooth Upgrades

Upgrade Rails 101: The Roadmap to Smooth Upgrades

This year’s RailsConf opens a new window 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 opens a new window

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 opens a new window 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 opens a new window

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 opens a new window 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 opens a new window , 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 opens a new window . 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 opens a new window .

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 opens a new window .

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

If you’re not on Rails 7.0 yet, we can help! Download our free eBook: The Complete Guide to Upgrade Rails opens a new window .

Get the book