It needs to have a much longer line from the gauge to the tip - maybe 12". Some valves are deep in the tire and others are on the inside.
With filled tires the valve has to be on top. If it is inside then it is doubly hard to deal with.
There needs to be an air release valve to:
1. Hold the pressure until you read it and then bleed off the pressure.
2. Bleed the air out of the tire if overinflated.