First of all, symbolicatecrash is rubbish*, but
before diving in and fixing it, make sure that your .app bundle
is in the same directory as your .dSYM.
Do you have dots or dashes in the app file name or identifier?
If so, you should apply the Alan Quatermain fix. It's intended for reading 3.0 crashdumps in a 2.x environment, but it also correctly handles dots and dashes in the app name and ID. Duh. Regular expressions am hard.
After that you're going to have to hack perl.
Try ./symbolicatecrash -Av mycrash.crash > /dev/null
to see where it's going wrong.
For my problem, I had to comment out both the quoteMeta($dsymdir);
and chop($executable); lines. Then I had something that vaguely worked.
And this was a shipping product. Welcome to the future.
As of *SDK 2.2.1, who knows, maybe in the 3.0 GM it's robust. It could happen.