Well first off thank everyone for helping me. I have the software running and am copying transmissions on the band. I can double click on CQ’s and if I enable the TX it appears to be sending. However, the radio does is not being keyed. I tried both 20m and 40m with similar results. I’m using the Sabrent adapter for Mac to the REM/Data port. Tx500 radio is in Digital mode. I did a time.is and the computer clock is exact.