Blake,

I don't have this radio or use this software, but here is a shot in the 
dark, so to speak:

I know that  when connecting my HF rig to the pc, either via Kenwood 
software, or any  logging program,  all the com port parameters  such as 
baud rate need to be the same both in the radio and the software.  Even if 
you are on the correct port but the settings aren't the same, the radio and 
software won't talk to each other.

These things usually turn out to be something simple, but can drive you nuts 
until you figure it out.

73, good luck, Steve KW3A