You basically have an electrical trouble shooting problem. Here’s what I would do:
1. Use a 12 volt test light or volt meter to make sure that when the truck is placed in reverse gear, that the fifth wire is energized. I think the order of the harness wires from the truck should be ground (male stud), head lights, turn signal, turn signal, reverse lights.
Don’t let the truck back over you when you test this. Even though the reverse lights work on the truck, there could be a connection problem from that circuit on the truck and your trailer harness.
2. If you don’t have a test light or meter, another trick is to turn on the truck head lights and make sure the trailer lights go on. If they do, you know you have current to that circuit. Then disconnect and trailer harness from the truck harness and take the fifth wire from the trailer (i.e. the right most male stud) and plug it into the left most female hole in the trucks harness (i.e. the hole closest to the ground stud). If things are working properly, you should hear a single click when you plug them together. This click is the reverse solenoid engaging which prevents the brake fluid in the surge brakes from reaching the brake pistons.
3. If you have energy to the fifth wire of the truck harness but the solenoid is not engaging (i.e. clicking) then the problem is downstream from there. It could be the trailer harness, trailer wire to the solenoid, problems with the connection to the solenoid, or a bad solenoid. OR… and I’ve seen this a few times with my set up which is the same as yours…. if I brake hard immediately prior to trying to go in reverse, it seems like there’s too much pressure on the solenoid and it will not engage to lock out the brakes. Try taking it for a little ride but don’t brake hard when you stop and see if it works.
Good Luck,
Boone