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One of the great mysteries: I put a larger flask on the CH2Cl2 outlet for the solvent system, thinking it still wasn't going to pull solvent (it hasn't worked in ~1 year). Started filling instantly.
If it was actually back siphoned it should have taken time to fill, so that wasn't it. Maybe it wasn't working because sometimes I have the system closer 6 psi rather than 9 psi? Could it make that big a difference for dispensing the heavier solvent?

I have no idea!