When I use my compression gauge I do let the air run out of the hose before packing it up, so maybe you do need to
I have some terrible news for you. I hope you're sitting down.
All this time you've been doing that completely wrong. To bleed the compression gauge when you're done you need to hang it upside down, otherwise the air will be trapped in the hose. Sorry to call you out like that on a public forum, but it had to be done.

