In case the "crash" is related to a die from somewhere within the code, you could use eval {} to catch the error.  If, OTOH, it terminates with a segfault, or bus error, or something, it would be more difficult to debug.  (If it was on Unix, I'd say set things up to get a core file to load into a debugger — but on Windows, I don't know how to get a core file...  maybe someone else does(?)).

Update: as an alternative, you might want to look into Unison instead — it syncs folders cross-platform in a convenient way.