I have never been able to get the Cakewalk problem reporter to work, did I say never ? . . . yes never.
It's not from never trying to get it to work, but I think the longest I waited one time was 30 minutes, went for coffee, sorry, that's my limit . . . time to reboot, restart. Is there a recipe to make it work ? I don't even know if the crash information ever got through to Cakewalk, I stopped caring about that years ago . . . though I always like to be helpful to Cakewalk to aid in fixing things . . . this just doesn't seem to be very useful, since there is never any feedback about the crash issue, or whether they actually pay any attention to it anyways. Reboot, restart, move on.
I will also add that my crashes are very few compared to what some others here on the forum are reporting, so for me it's really a non-issue . . . still, if it's a feature, it really needs fixing . . . if it doesn't work for so many years, delete it, save us all some time.