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answers:

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Is there a way to tell a running "script/server --debugger" to pause execution and open the debugger prompt (other than sticking a "debugger" statement in my code)? Similar to CTL-C in gdb.

I would like to do this, so that I can set a breakpoint in Base.update_attributes without having to put "debugger" in my own function (and having to hit "n" every time my function executes).

A: 

Not sure about a direct answer to your question, but you could use Jamis's solution for GDB here: http://weblog.jamisbuck.org/2006/9/25/gdb-wrapper-for-ruby

Tim Rosenblatt
Interesting link.Eventually, I've just handled it by putting a 'debugger' call in the Rails source, instead.
korinthe