I find two common issues with rudder tubes – which does not mean that either of these are applicable in this situation, of course.
1 – the point where the tube exits is not a flat surface. Typically, if the 'V' of the hull flattens towards the transom, there is usually a slight 'V' at the point where the rudder is.
2 – the rudder tube is only secured at the base of the tube, while the tiller provides sideways forces at an inch or three above this. If there is a thick keel this can be OK – if not the base of the tube will tend to flex under load and eventually leak.
I usually address these issues by making a flat at the rudder exit and epoxying a washer in there, and providing support half-way up the tube. Easier to do if you're not using a made-up rudder with a screw fitting….