So how does one report a problem when the problem reporter reports that it has encountered a problem? Hehehe.

 
I don`t believe I have ever managed to send a report.  

when you click yes, a crash file is sent to cakewalk.
I believe those are stored in your app data file/temp directory.

I have reported MANY MANY issues this way. However, despite the option that says "Keep me updated by email on this problem" or whatever, I have never gotten any emails back from it. Quite possibly the email goes to an email folder marked "Hopefully the user forgets about this soon" in the Bakers' kitchen somewhere..

Of course, that was when the Problem reported was still reporting. Oh, how I miss the glory days..

The problem reporter always fails to send the crash log before 'encountering a problem' itself!

I have sent several dump files this way and gotten acknowledgement emails back.  Things do seem to freeze up a bit while the dump file is created.  I wonder if possibly tou are canceling the task while it is creating the dump file?