Unable to hit certain breakpoints in Docker App

I am using IntelliJ Ultimate 2018.1.4 with ruby plugins, but I've also encountered this same issue in RubyMines.

I am able to successfully connect to my docker container running a Rails 1.2.6 application. However, it seems that I can only hit breakpoints set in the bootstrapper file  boot.rb; Breakpoints in controllers following a web request are all ignored.

Additionally, the last execution of that file is 


Oddly enough setting breakpoints in that run function is also ignored.

Are there any ideas of where things may have gone wrong?

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