I can add a bit.
The issue I usually have with these is that the programming cable doesn't always seat all the way in the jacks. As Daniel said, give it a little push. Often the weather sealing makes it a little difficult to get it to seat all the way.
If the software isn't doing anything, no errors, nothing, then it's usually an issue with the connection. Either the cable isn't seated all the way, the wrong Comm port selected, or the jacks on the radio are damaged.