Dully,
I don't have a Winegard satellite system, so I probably can't help too much. (I have a Tailgater on Dish.) I think Winegard makes several different satellite systems. Which one do you have?
If it is a portable one, try running the cable through a window directly to your satellite receiver, and from there to the TV. It's easier to get it working that way, before you try to use the trailer's cable system.
Is it an auto aiming model? Is the problem aiming the dish at the satellite?
You do have a receiver from Direct? Right? Has it been activated with Direct?
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Mark S.
2014 Cougar 318SAB
2015 Silverado 3500HD 6.6L Diesel 4WD CC SB
18K Pullright Hitch
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