Any extra command-line options that I should put on winedbg to help find out the problem?
no. it seems however that: - debug info is not found. Either you did remove -g flags from compilation, or you have two wine trees (or installation), and lookup isn't done on the right tree (install) - your application dies before the debugger did finish its startup. you could also try to run your app from the debugger (winedbg your_app instead of wine your_app)
what's strange however, if your wine always crashes at startup, how come winedbg can actually start up. something's really strange in your configuration
A+