Hm, you've added a single breakpoint and the debugger stops at it.
Why are you saying that it fails to do so?
There is some mess after the info frame command.
Can you disable the function arguments and locals, so there is less noise in the output.
And also it is a bit safer without evaluating them.
Have you tried to debug cb.exe using command line debugger to verify that the gdb build you're using is working fine?
Also can you execute info breakpoints and bt 30 manually after the debugger stops on the first breakpoint.
p.s. I have nothing against win 64bit build, just I have no intention to work on it, because it is on the wrong OS.
p.p.s. I'm not sure if it is really good idea to pursuit cb 64bit+wx2.8.12. It will probably be easier to target wx3.0 directly.
p.p.p.s. Hm, but at work we are using minimal parts of wx2.6/2.8 in 64bit apps on windows with vc++/icc and there are no major problems.
p.p.p.p.s. My intention is to help, not be rude, sorry if I've offended you.