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answers:

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

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

A: 

Firstly, make sure you build with source debugging enabled (the using -g option):

gcc -g -o myfile myfile.c

Then Load the dump into gdb after the crash (or insight, or ddd)

gdb myfile core
BenB
Stackdump != Coredump
Gerhard
+2  A: 

You can instruct Cygwin to start your gdb debugger just in time when an 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"

Gerhard