This advice straight from Iwata/Medea- It could be one of four things:
1. The fluid needle head needs to be sealed (either with their Super-lube or a non-drying wax on its threads)
2. Turn the needle clockwise a couple of times to seat it in the head- sometimes they don't mate perfectly.
3. Cracked needle tip. I was warned that machining them down past the flaw only makes them look nice, but they remain non-functional.
4. Bad o-rings. Don't soak the thing in solvent!
Hope this is informative and helpful! Thanks to those who offered help.