Is it possible to programatically set a breakpoint... that is... start the debugger, that RubyMine uses, ruby-debug-ide?
My goal is to somehow start it automatically when a test fails.
Programatically set breakpoint for ruby-debug-ide (RubyMine)
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I was looking for something related this when your question popped out. So what you want to do is to break when certain (or any) test fails? For this purpose you can use the debugger command.
Just add begin...rescue block to your test as follows
If you aren't using the Minitest, replace the Minitest::Assertion with the appropriate one such as Test::Unit::AssertionFailedError for Test::Unit.