I've also had various occasions where code compiled successfully but no longer worked as intended.
Put another way, automated test suites give you an extremely high level of assurance when using a statically typed language. When your test suite passes in the new version Ruby, you're happy but there still could be cases left that you've not dealt with in rarely triggered code paths/conditions.
The costs of static typing are reasonable as long as you're not using a fancy dependently typed language. Ask companies that are maintaining long running software -- types help. The investment is there in the beginning, the payoff is over the lifetime of the project.
If types are complex and poorly defined, you can change them ! The compiler will help you evolve your system through type errors. If you have a poorly structured program in a dynamically type language like Ruby then it becomes more difficult to evolve your system fast and with confidence. You're always asking -- have I missed something out ?
Ultimately, I think that choice of language is one of the least significant predictors of outcomes, yet it's one of the most debated and obsessed over.
Edit: I thought it would be helpful to give examples of what I think is more important. Good CI/CD practives, good observability, robust test and staging environments, etc have been far more important in my experience than static vs dynamic language choice.