Here is the Parts diagram:
This is the plunger (circled in red above):
Here is the type of filter I have in mine (Norgren 3652-11):
Notice it's different from the one shown in the parts diagram. Maybe it's a newer style. But what I see happening is the plunger moves up and the little stem comes out of the O-ring. The plunger then "tilts" and won't go back down into the O-ring to seal. Maybe the newer filter allows the plunger to move up too far?
I removed the plunger and the little O-ring from the canister. You need to push up inside from the threaded nipple on the bottom of the canister to pop out the o-ring. Then just screw in a tire Schrader valve (up from the bottom) inside the threaded nipple. I had to remove the o-ring because the Schrader valve got stuck on it in the open position. Insert Schrader valve in here:
I figure the filter will still "filter" the air and I will just open the valve when the system is pressurized and let some air out (like airing down a tire) and it should blow out any contamination in the bowl.