Return gasket replacement

I had an above ground pool installed last year. The installer put two returns in. One just below water line and one about 2' from the bottom. The lower one has had a leak since day one. It leaks to the outside between the outside threads of the body and the big retaining nut. That must mean it's leaking past the gasket inside the pool.

The pool guy came out last year and spread some two part epoxy over the nut that he must have hoped would magically cure the leak. Obviously that didn't work. He never did come back out last year to fix it again. It was a slow drip, so I just let it go.

Over the winter it seems to have worsened. I asked him again to come out and he said it would be no problem to fix even without draining the pool. Great, but he never showed up and won't respond to calls. So I'm on my own. Does anyone have any tricks for this that don't require draining half the pool? I could loosen the outer nut, push the return forward (into pool) enough to stretch the gasket out and over the flange. Some water will leak no matter how quick I do it, but will the potential flood of water shift the liner?

Or should I just bite the bullet and drain it?
 
If the leak is caused by the external assembly: Assuming that it is a Hayward return eyeball fitting (or that there is some standard threading). If you unscrew the eyeball ring and then the eyeball adapter ring only (not the return and gaskets itself) you should be able to screw in a Hayward ball valve from inside the pool (or use a threaded cap, or plug the eye). Then you will have to have someone pushing this assembly hard from inside the pool while you replace the outside gasket. However, it is likely you will lose some water during the process.

Since you state it is most likely the internal gasket, can the nut of the assembly be tightened any? On the other hand, is there any evidence the return has a crack, since the water is also escaping the outer gasket rather than between the liner and wall. If the return can be blocked on the pool inside and plumbing removed does it still leak?
 
You can have someone hold a large bowl over the fitting from the inside of the pool while you work from the outside. I would get a new fitting and gasket since he glopped epoxy on the current one. Since this one is down low you may need two helpers to hold their breath and tag team holding the bowl over the fitting. You can also try inserting a plug in the fitting and see if that stops the leak. You don't need a lower return and its kind of odd he put one in at that location.
 
Since you state it is most likely the internal gasket, can the nut of the assembly be tightened any? On the other hand, is there any evidence the return has a crack, since the water is also escaping the outer gasket rather than between the liner and wall. If the return can be blocked on the pool inside and plumbing removed does it still leak?

I've tightened it more to the point it's starting to spit the outer gasket out. There is no exterior evidence of a crack, I can't feel anything on the inside, but I haven't put a mask on in the pool to check it. I'll try blocking it with toilet plunger and see if that cuts off the leak.

It's hard to make out in the picture, but it's coming from threads. No leak at the external gasket. It's most likely leaking between the liner and wall, but no visible evidence of that, but I guess I don't want it to get that bad.
 

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If it’s from the threads and not around the gasket, it’s an easy fix. Remove the eyeball fitting, insert a closing plug, removed the Union before the threaded male piece. Apply liberal amounts of plumbers paste and retighten.

if it’s the actual return fitting, I would recommend this. Buy a new return fitting, notice it will have two rubber gaskets and two cork ones. Remove eyeball, plug and remove the Union and threaded fitting as above. Take part of return fitting that goes in from the pool side, slide on cork and then rubber gaskets. Insert a closing plug. Remove the locking nut on the one in the pool, hydraulic pressure will stop an onslaught of water rushing out (there will be a good leak now. Jump in pool, quickly removing old one and replacing with the new one. Once outside pool, slide rubber gasket on, then the cork and finally the locking nut. Tighten as hard as you can by hand. The cork allows it to rotate without binding up on the rubber. Once secure, follow plumbers gunk on the fitting that screws into this as above.
 
If it’s the actual return fitting, I would recommend this. Buy a new return fitting, notice it will have two rubber gaskets and two cork ones. Remove eyeball, plug and remove the Union and threaded fitting as above. Take part of return fitting that goes in from the pool side, slide on cork and then rubber gaskets. Insert a closing plug. Remove the locking nut on the one in the pool, hydraulic pressure will stop an onslaught of water rushing out (there will be a good leak now. Jump in pool, quickly removing old one and replacing with the new one. Once outside pool, slide rubber gasket on, then the cork and finally the locking nut. Tighten as hard as you can by hand. The cork allows it to rotate without binding up on the rubber. Once secure, follow plumbers gunk on the fitting that screws into this as above.

Just as a follow up for anyone ever finding this in a search. The above is the way to do it. I probably lost maybe 1 gallon of water when I actually swapped the fittings. Worked great. Now to fix the 3 piece pvc union I broke tightening it back up.

The root problem was that the return fitting was cracked where the 1 1/2" pvc to threaded adapter was threaded in.
 
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