What you may be missing is that the cups (the rubber seal between the caliper bore and piston) are specifically designed to seal against pressure from one side only. They are tapered in towards the fluid side. When pressure is applied it actually works to press the rubber seal against the piston (or in some cases the caliper bore). The harder you press on the brakes the harder the fluid presses against the rubber seal and the tighter the seal is. Very effective.
However, it works in the opposite way from the reverse side (the air side in this case). If you looked at the seal you would see what I mean. I could not find a good picture of what I'm trying to describe so I made one. Pretty ugly I'll admit. But if you can get by that I hope it demonstrates what I'm trying to describe. The seal can go on either the piston or the bore. This picture is a piston mounted seal but it's the same thing either way.
The seal goes all the way around the piston, of course. But for demonstration purposes I just show the seal as 2 tapered wings (plus the fact that I can't draw well enough to do more than this anyway). The clearance to the caliper bore is much less than this and distorts the seal somewhat.
As you can see, when fluid pressure is applied it pushes against the rubber expanding it against the bore giving a great seal. The opposite effect is true when pressure is applied from the opposite side. Any negative pressure inside the caliper will try to equalize by pulling air past the seal. It takes a relatively small amount of pressure differential to allow air to sneek past the seal. The seal simply is not designed to seal against much pressure from the air side. Nor does it need to in a properly working system.
The other problem here is that soon, Lamontster is going to tell me to take this to the Tech forum! :joke: