With the automated debugger tests, it seems that the timeout is being hit with every test, regardless of whether or not data is matched correctly. I gathered the following statistics with variable timeout values for 15 tests:

parser
timeout 5 sec - 122s
timeout 10 sec - 131s
timeout 20 sec - 132s
timeout 30 sec - 148s

debug
timeout 5 sec - 77s
timeout 10sec - 152s
timeout 20 sec - 303s
timeout 30 sec - 452s

The timing for the debug tests is very consistent. Running the debug suite with a 5 second time out took about 77 seconds every time. The execution time increases by the same degree as the timeout. The CLI debugger isn't exiting correctly, so the test does not end until the timeout is reached.