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 

Rails::Initializer.run(:set_load_path)

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

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