Could be your compressor isn't big enough or your tank is too empty.
With a full tank even a small compressor will work.

You could also have a return line leak inside the tank that doesn't effect engine performance but when you pressurize the tank it pushes air up the return line.
Pressurizing the tank fills the filter from both the return and feed lines.
A fuller tank may cover the leak and allow things to work right.

Be careful with a very full tank though. When you relieve pressure at the tank you can end up taking a diesel bath.

 

Thanks infidel, I will try it again next filter change.

Floyd

 

Infidel's pressurizing the tank has worked for me sometimes, and other times I've had Blackimpala's experience, so maybe I have that return line leak in my tank. I'll pay attention to how full the tank is and see...

I keep the hoe handle in my truckbox, has come in handy when I ignored
my "empty" fuel gauge before (shame, I know)

 

Infidels technique works great and if you have a problem, just pinch off the return line. I'm in his camp, haven't used the primer button since the 90's

cd