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Debugging in CygWin environment

So I wrote buggy code that occasionally crashes ... and creates a stackdump file.

Using addr2line I can figure out how the program got to the crash point
by decoding the addresses one by one. Is there an alternative tool that
can ease the debug using stack dumps? Is there a way to load this
information in Insight/Gdb?

You can instruct Cygwin to start your gdb debugger just in time when
a fault occurs. To achieve this, add error_start=action to the Cygwin
environment variable:
	   export CYGWIN="$CYGWIN error_start=gdb -nw %1 %2"

Else you can have Cygwin generate a real core dump.
	   export CYGWIN="$CYGWIN error_start=dumper -d %1 %2"
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