I have the same issue going with my 2020 Trail Boss. Tried a trailer and no lights, tried a lighted hitch cover and nothing. They tried tell me that the items do not pull enough power. As a trouble shooting step I asked them to take my pig tailed wiring harness that allows me to have a the 7 pin connected to the bumper while giving me a 4 pin flat connector to another 2020 truck. They did and it worked perfectly. However, my truck has the "upgraded" tow package that includes the camera views and everything. The 2020 truck that it was tested on where it worked perfectly had the tow package one step below mine. So, in short the package that has a 4 pin built into the bumper of the truck as part of the 7 pin connector, your accessories and older trailer will work. If you have that same truck with all the camera views and the top two bumper mount connections in your left of the plate bumper mount are camera connectors and not the 4 pin, you will have the problem of the lights on an old trailer with 4 pin not working and neither will accessories that are powered by that 4 pin. The high end tow package has issues. The techs were able to get it working when you first turn the truck on, but as soon as you press the break is pressed the connections stop working until you turn the truck off and back on. There is a sequence somewhere in the line that probably needs a dummy load or some type or a different type of power draw regulator. This is hopefully going to be in a software flash or factory recall, SOON I hope.