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I recently bought a townhouse built mid to late 1960's. Just moved in so have no real time in the place yet.

Yesterday, I had a clogged toilet incident in the second floor bathroom. I have since manged to unclog the drain after many flushes and much lye drain cleaner. A plunger session finally did the trick after 24+hours.

Before finally freeing the clog, I found water dripping from the first floor ceiling beneath the bathroom. Quite a bit in fact, do to the numerous flushes I did trying to free the clog.

None of this is particularly surprising or odd, but my question is this: Should I assume the floor seal is bad (or at least marginal) based on the water in the ceiling and just go ahead and replace the seal (not a job I'm looking forward to) ?

The water in the ceiling did NOT come from any overflow on the floor up stairs because the water never overflowed the toilet. I've done seals before, but what I'm really asking here is, if the seal is good and functioning properly would water from the waste stack ever leak into the ceiling ?

Just not sure about this. Does the water in the ceiling indicate a bad seal or is this normal given a clog and a bunch of flushes (again, no water ever reached the floor upstairs )?
 

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Yes, replace the toilet wax ring. Sounds like the stopped drainage pipe and the pressure caused by the repeated plunging forced water out. Will take some time for that water to find its way down though the ceiling below.
Next time use a toilet auger.
 
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