No worries, Paul, just stick it in the hole and crack the valve open, that air will figure out where it needs to go :-). Just make sure you fill SLOW, bleed FAST. I would suggest you keep some pure silicone grease with your fill station, and lube the orings on the adapter frequently. Just a touch between your thumb and forefinger, then wipe it on the orings. I use silicone dielectric grease from NAPA, divers silicone grease works too.
If you look inside the port on the rifle tank, there's a small hole on the action side of the air tube. That's where the air goes, the orientation of the fill probe doesn't matter, there's enough clearance around it for air flow. It always seems to me like the fill probe should blow itself out, but it works fine. Hope that helps, if you need to, give me a call, 509-429-0548.
Dave