Now @thomascountz is giving a talk "From #Legacy to Latest: How #Zendesk Upgraded a #Monolith to #Rails 8.0 Overnight" at #rubycommunityconference.
Also, it's not very obvious in the photo but the slides have an amazing console #ASCII style. 
The bigger the framework, the harder the upgrades. Back in the day, I never expected to see talks about just upgrading or maintaining projects (ActiveRecord encryption + ActiveStorage).
Today, upgrading my simple Rails API to Rails 8 was a pain. So I set a goal — before Rails 9, I’m switching to minimalistic #Crystal and its Web frameworks. No more #Rails 
.
It was a good ride for almost 20 years.
@miry I don't think that framework needs to be a factor on this.
I think a framework can be big or small independently of having easy or hard upgrades.
However, additional dependencies, usage of internal APIs, forks or mixtures of coding patterns might influence this a lot in my opinion.
Especially recent Rails upgrades went pretty smoothly for me.
@miry @alexanderadam There are simpler frameworks in Ruby too. Hanami comes to mind. But a simple app should not have big problems upgrading. Perhaps you’ve coupled yourself too much to the framework - which is understandable with Rails.