When I set a breakpoint in a shoulda context/should block, ruby-debug reports the wrong file (but right line number)
when the breakpoint gets triggered.  If I rename the test to a method definition, it reports things correctly.

Original issue described here:
http://www.jetbrains.net/devnet/message/5261044#5261044

$ gem list | grep debug
ruby-debug-base19 (0.11.23)
ruby-debug-ide19 (0.4.12)
ruby-debug19 (0.11.6)

Date: 2012-04-12 15:29
Sender: Brian Levine

I see related behavior trying to debug RSpec tests in Aptana
Studio (Eclipse) with ruby 1.9.2.p318. Apparently, RubyMine works
around these issues by including its own patch
to ruby-debug-base19

Date: 2010-11-01 23:14
Sender: Chris Williams

Note that this issue is still present in ruby-debug-base19 0.11.24
with ruby 1.9.2p0, is in no way limited to Shoulda (I've had
it happen while debugging several different gems), and affects
both ruby-debug-ide and ruby-debug-ide19 when using both Netbeans
and Rubymine. There are multiple posts in both the Netbeans and
Rubymine forums with users experiencing the same behavior (right
line number but wrong file reported for current code position).

I'm using RVM, which may be relevant..not sure if other users
having the issue are or not.