I have a 20x40 IG vinyl pool with 2 returns in the steps. When the returns were installed, the pool contractor did not have the pipe drop down 90 degrees and lay on the concrete ring. Instead, it was a straight run from the back of the return. Pool was installed in 2004 and over time, as the ground settled under the concrete deck, the pipe was pulled down and cracked the return fitting at the body and flange of the fitting. I epoxied last year but decided to go ahead and replace. I cut out the concrete and exposed the pipes. Drained pool down below the fitting, cut out the piping and replaced the fitting. The type of return fitting is the ones that is secured with a large plastic nut and has 2 rubber gaskets and a cork gasket. Before installing I cleaned both sides of the steps where the fitting goes and made sure the step surface was smooth. I tightened the nut a turn or two past hand tighten and filled pool back up. It began to leak behind the fitting was water covered the fitting. I tightened the nut some more and still have a leak. Anymore tightening and I will probably strip the threads. The gaskets were installed with one rubber gasket on the inside of the steps, one rubber gasket against the outside of the steps, and the cork gasket on the outside between the nut and the rubber gasket. I did not put caulking on the gasket that is on the outside of the steps. A local pool supply store said that is typically done but my thought was that the rubber gaskets should be fine to seal. So, should I caulk the outside rubber gasket and replace and if I do, will I need to drain pool again?