Replacing Return Fitting in Steps

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?
 
Are the steps fiberglass?

The seal should be the inside gasket surfaces. It should seal even if the outside gaskets weren't there.
Did you caulk both sides of the inside gasket?
If so what type caulking did you use?
Did you allow plenty of time for the caullking to cure before disturbing it?
Are you sure it's a gasket leak and not a fitting leak?
 
Steps are fiberglass. I am pretty sure it is a gasket leak. After I first replaced the fitting and it leaked, I bought a second fitting and replaced to be sure. I did not use caulk, should I? If I should use caulk on the inside gasket, I will drain pool down again and reinstall the fitting.
 
I thought the cork gasket goes on the inside? (that's how I did mine - plastic, then cork, then plastic, then return, then another plastic gasket on the outside.)

My return fitting has this adapter piece screwed into it, and it's had a drip there for the last three years. We finally took it apart and put teflon tape on this part before attaching it to the return fitting. Drip stopped.
http://www.flexpvc.com/cart/agora.cgi?product=PVC-Swimming-Pool-Adapter
 
While the gaskets should seal without caulking, a lot of times they won't (as you've found out). I would use a good marine silicone caulking on both sides of the inside gasket and let it cure before raising the water level back up.
 
When replacing a liner I hardly ever caulk, but you need to be careful with the gaskets and plastic strips make sure they lay flat and out of the sun so they don't become distorted. Never had a step gasket leak yet that we installed; the strips of plastic should sandwich the gaskets together to make it water tight. Using a silicone to make something stop leaking isn't really addressing the issue of why the gasket isn't sealing (stripped or damaged ferrule or screws) etc.
 

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I have vinyl liner pool with a leak. I had someone check the lines and he said they all checked out but one return on the steps. Is there an easy way to fix this. He wants over $2,000. to fix it. I am getting other estimates, but I thought someone from this site might be able to give some information and advice. Anybody?
 
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