[...]What does this actually look like? Is the water coming out of the liquid out post?
I snap a beer QD with some tubing on it to run back to my Star San reservoir.
I don't have the ability to do a closed, pressurized transfer from carboy to keg, but will hooking up the auto-siphon to the liquid post work?
Filling the closed keg through the liquid post is always a good idea, even if you're not doing a CO2 push. Given enough height from your carboy down to the keg, once you get the flow going it should work ok...
Cheers!