Tub Drain Leaking... Still

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Long time reader, first time poster. Thanks for all the great information on here. Here's my problem: updated the tub/shower with new components: shower head, tub spout and pop up drain. Spout and shower head all good, no issues. However, for the life of me I cannot get the drain to seal properly.
The old drain was a basic pop up (toe operated), rubber gasket only between drain and tub, and underneath was another rubber gasket to the drain pipe flange, which was just a 1 1/2" threaded SCH 40 adapter, no flat flange for gasket to sit on like a shoe does. This hasn't leaked for the 2 1/2 years I've been in house. There is no overflow in use.
-So first, I tried installing new drain and new gaskets (also toe operated pop up) same as the one I took out; rubber gasket between drain and tub, and rubber gasket between bottom of tub and drain pipe. No dice. Tried repositioning a few times but still leaked. Got to the point where it felt as if something was going to break and it still wasn't sealed so I gave up on that. I did try old gasket just for haha's but no better.
-Next, plumbers putty between drain and tub, rubber gasket between tub and drain pipe. Better, but still no go. Redid this a couple times to rule out not enough of too much putty, still no better.
At this point I decide to swap to a shoe drain as I am not confident I will get it to seal with the gasket just sitting on top of the threaded adapter that is in place underneath. Not sure how it sealed in the first place but that is besides the point.
-Now, PVC shoe drain installed, new gaskets top and bottom. Still leaked, but not nearly as bad. I've heard many mixed reviews on gaskets and being an older looking tub I decided to give Putty a shot. Ran a full shower through it. Much better, but it did have a couple drips around rubber seal underneath still. Verified it was tight, sitting straight, gasket seated correctly as I can see. At this point, I'm sick of dealing with it and caulked around the edge of the drain in the tub.
This helped, as this morning after a shower the rubber gasket under tub is visibly wet, but not dripping.
All I can think of now is, the water coming up through the threads between drain itself and the shoe somehow? I don't feel confident trying to tighten drain any further without breaking it.


The Plumbing Wizard
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Bothell, Washington
Normally the rubber gasket by itself is enough to seal between the bottom of the tub and the shoe. Alignment is important there. Any angle can let water past. Sorry this has been such a problem. Is the bottom of the tub smooth?
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