You're right on the ragged edge of where the TL431 will opeate. I think you'll want to see 3+V on Kreg, but we can now see that it's over 1V, so the 12AU7 cathodes are spewing some electrons.
I'd swap in another 12AU7 or two and see if you can get that voltage to pop up a bit. If all your 12AU7's are behaving in the same manner, I would replace the TL431 regulators (I've blown my fair share of them, they are an amazing chip, but somewhat sensitive).
-PB