Air lines with a headache rack

I have this same problem on my truck. Actually have it set up the exact same way u do. Couple of our drivers have the pogo sticks and they work good . Me im lazy and just put a couple layers of electrical tape on the lines where it touches the headache box.

 

@Kyle G. looking at the pic I think you are safe because both contact points are already double protected (heavy pvc spiral wrap and rubber zip-tied on top).
You can also take a 12" to 18" piece of split heater hose and glue it to your tray edge and lid so that you have 5 to 8 inches on either side of the hose contact point. I suggest contact cement for glue.

 

You could move the spring attachment 6" closer to the trailer to keep the hoses further from your walking deck.
A pogo stick is not a good idea if you may put a small front overhang on the trailer with your frame length.

 

I don’t have a picture because I don’t run my airlines like im about to suggest anymore. I would suggest that you take the extra slack that you have zip tied to the base of the cord and run that excess in a loop between the two springs off the pogo stick. That way, as your trailer gets away from the truck turning at an angle, the Outerloop of slack can stretch further out on the spring and therefore not put undue stress on the airline itself.
i have had exactly one sip of coffee this morning so far. So I might have to come back and reexplain this?

 

You did all that at a Kwik Trip????

 

Like this? You’re a smart man! Ignore the extra light cord and the way to long line. That will be fixed next Time I’m home.