Hmm it is not the liquid beer changing volume that impacts the headspace pressure. 20 Liters of water at 20 C will still be just about 20 L at 1 C. Actually if I did the math right it would be 19.9661 liters at 1 C but think you can see that change is not really driving a measurable pressure change (measurable with typical conical pressure gauge at least).
Instead the gas in the headspace changes pressure as described in the ideal gas law pV=nRT;
where p is pressure, V is volume, T is temperature, n is amount of gas and R is gas constant.
As mentioned above Volume of the gas in the headspace can be treated as a constant at beer relevant temperatures. R is also a constant so you can see pressure in the headspace should increase if either temperature increases or n increases (from generation of fermentation gas). Likewise if you cool the gas in the headspace or release gas from the headspace pressure in the headspace goes down.
@T Murph sounds like you have not yet solved the pressure holding issue. Suggest running a pressure test once you finish this batch with empty fermentor. You should be able to pressurize to 10 PSI and it should hold that pressure. Just make sure you are not changing temps in the system while you are trying to understand if you are holding pressure.