I got a response from Heroku support about this.
Everything I did was correct, the problem is the application boot errors won't display to the screen, and this was a boot error. The source of the error was further back in the backtrace in heroku logs
, so that was in fact the right place to look in this case, I just missed it.
Setting RACK_ENV=development
is the correct way to display application runtime errors to the screen, according to support.