Originally I did not use dielectric grease or the provided waterproof connector. With the placement under the eave and attached to the soffit I didn't think it was necessary. There was a small gap in the flashing in the corner of the roof, where where the gutter, drip flashing, and facia flashing all come together. That gap faced the predominate wind direction and we have had some very heavy rainfall with high driving winds. I also had some excess wire looped up in the soffit and it was touching the inside of the cavity right behind where the gap was. The box was over 12" away from that gap/hole, but the wire just happened to be in the worst possible location and allowed the water to run right along the wire into the box. I sealed up the gap, moved the wire away from that area, and used a waterproof grey PVC box connector on my round terminal box, then ran about 6" of the flexible grey conduit up into the soffit cavity. I don't think it would be possible for water to get in there again.
For future use, do you just put a squeeze of dielectric grease inside the RJ45 receptacle before you plug the connector into it?