I had a difficult time on a few tires getting air into the tire. I decided the air chuck may be the issue? So, I replaced the inexpensive chuck bought from an auto parts rack with a straight-in $14 chuck from a truck parts store (napa has too if ask for it).
The first time I have used it, three tires aired much much easier. So pleased it made that difference, at times almost gave up with the cheaper chucks.
If you have trouble getting air in a tire even with 150 psi, you may consider the chuck change might help.
I believe this is what Mike is referring to:
Yup. Chuck knows chucks all right!! >:D >:D
Chuck is (almost) my middle name!
Seriously though, I use and recommend the "straight-in/straight-out" type chuck, and it works great. Especially nice for the inner valve on the rear duals. After a bit of practice, I can literally find the inner filler with my eyes closed - it's that easy.
Only downside, at least with the one I use, is it does not "lock" on the filler stem. Must be held in place by hand while using. Some may consider this a disadvantage. For "topping off" the tires one or two psi, I don't feel it is a problem. If I was faced with refilling one of these big tires from zero psi, I would certainly want a locking chuck, both for safety and for convenience.