So I changed the name of this thread on my phone so I could post to it from work without that previously ridiculous title I picked out of frustration.
So, to clear a couple things up, my carboy was on top of my fermentation freezer and the keg was on the ground...it's how I always transfer and has always worked in the past when I wasn't so obsessed with the idea of a closed transfer. I had been dry hopping the beer at 60 degrees so it was relatively cool and I do use pin lock kegs, but I pushed down on both of the connectors when I thought the transfer should be happening, but nothing was happening.
So, the reason I was so focused on a closed transfer is because this is my first lager and it's going to sit in the fridge lagering for a couple months so I wanted to do everything I could to not expose the beer to any air/O2 during the transfer.
What I did was fill the keg, clean it and all its parts, put the dip tubes in, posts on, lid on, still full of starsan solution and then pushed it all out with CO2, I then hooked up all my tubes and went to work.
What I think happened is that when I hooked the keg connector to the beer out side of the keg to transfer the beer in, the keg was still pressurized at about 12PSI and as soon as I connected it, it shot CO2 into the carboy through the racking cane straight to the bottom of the carboy and stirred up the 4oz of settled hops in there I had been dry hopping with and I'm guessing some of that stuff clogged the connector on the keg causing the beer to not transfer.
So I just ended up removing the keg lid and unscrewing the hose off the end of the keg connector, putting it down to the bottom of the keg and transferring that way...like I always do.
I guess I don't know what an Auto Siphon is....I usually transfer using my stainless racking cane, a carboy cap and a sanitary air filter. I hook it all up, run the tube from the end of the racking cane into the bottom of whatever I'm transferring into, pinch off the tube near the racking cane, blow into the sanitary air filter, release and the transfer goes without issue.
I have a racking cane sock (mesh thing) to go over the end of my racking cane on order so in the future this should help keep hop material out better than the little caps on the end of the racking cane I've been using.
So there you have it.
Thanks for the help so far and I guess I'm just lucky that the 12PSI I was transferring with didn't blow the carboy sky high

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Jamil Zainasheff has a walk in cooler.
Pamela Anderson has a walk in cooter.