Chimney condensation? Any experts out there?

I would recommend not getting a liner for your oil flue, it serves no safety purpose and even the best 316 stainless will fail in the future causing you more problems that you would not have.
Well, that didn’t work. The repairs/adjustments he made to the chimney flashing, and crack up top didn’t do anything when it was cold and rainy yesterday.

I ended up getting a drill and drilling a hole right through that’s plywood to get a look on the other side. Theres a vapor barrier and it looks like that plywood is right up against cinder blocks? I mean that’s where the chimney is, but on the side facing the house it’s cinder block? Because I definitely hit cement, could see the cider block. The play wood is maybe a 1/4 inch away from it (figured it’d be at least an inch, but no, it’s right there). Doesn’t really seem wet on that side, but hard to tell.

It’s wet to the touch inside. The water is visible inside. Starts up top inside, and slowly weeps downward. Is this condensation?? In the back of my mind it’s what I initially thought it was. People are saying to me...there’s no way that moisture is wicking from the outside of that plywood and coming through. It’s inside. Yet there are no leaks above it. Nothing. There’s a gigantic high ceiling room under that attic space. Am I losing heat and it’s going up that wall? Can insulate that wall and floor and see improvement? Really don’t know what to do at this point. My estimate for the liner was $2,600.
 
As I mentioned earlier, there's really only two good possibilities or a combination it's either leaking through the cracked mortar, crown, and the brick work and slowly seeping back through to the plywood AND/OR it is a leak from the roofing / flashing.

I understand the reasoning behind your thoughts on condensation. However, that seems very unlikely. Something is dripping or seeping down from above in a way that is not redily apparent. Leaks are often very tough to pinpoint a source; This is why I have been trying to encourage you to keep investigating vs. liner etc which will leave you with the same problem you have now.

The fact that the masonry does not seem to be wet behind the plywood - if I understand you correctly - means that the leak is coming from the top down which indicates that the shingle / flashing interface or thereabouts is the culprit.
 
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Just an update.

Had the chimney reflashed and sealed. Did nothing. Still had water building up on the plywood inside the attic.

Had a stainless steel liner installed last weekend - believe me I didn’t want to - and it appears to be doing “something”. Hard to tell. But it doesn’t appear to be building up in the attic anymore. It looks like it is trying to dry itself out. Lot of leftover staining, mostly white and crusty. Seemed to be getting some sap out of the wood too.

The guy that installed the liner is also the guy who flashed the chimney for me, he said he immediately felt a difference when the liner was installed. That heat was actually coming out of the TOP of the chimney, whereas as before he could feel almost nothing coming out...that the heat was building up inside the chimney walls and condensing. His thought. And he said the flow and the heat coming out of the top of the chimney now is very noticeable, compared to before. Who knows? All I know is that the attic doesn’t seem to be getting wet for the first time since I turned the heat on back in late October. Hope it’s fixed, this has been a long long time coming now. i must have called 15 different masons and chimney specialists, no one called me back. Just this guy.

It snowed the other day, before the liner was installed this is what I’d normally experience...melt. Melting at the roof around the chimney. Melting almost instantly on top of the chimney itself. Now? Nothing. Snow is not melted around the chimney on the roof. Snow has not melted on top of the chimney itself. Perhaps the heat is going where it’s supposed to now? Out, instead of in? I hope so. Fingers crossed.
 
One other thing, the guy applied Crown Coat to the top because I asked him to. The stainless steel cap has been on back order, and he'll be back in a couple weeks to install it when it comes in. But, knock on wood it does seem better at this point.

I really didn't want to do this liner, I'm not convinced the liner has fixed this thing yet, but there does seem like improvement. Thank you for all the suggestions and believe me the people that said not to do that liner...I trust your opinion 100%, it's just that I had run out of options. It was/is nearly impossible to get someone to come out in the middle of winter and handle something like this, so when that one guy is telling you "it's the liner" , and he's standing there in front of you telling you it's not the flashing, it's not the crown, it's the liner. You're kind of out of options.

But watch it just be the $120 dollar crown coat that he applied (after I asked for it). I'm selling the house in a couple years, I'm done with this thing. Almost $1,000 spent on oil last month alone. This isn't for me.
 
yup, probably the crown. I've built and rebuilt many chimneys that were having similar symptoms, It has never once been the liner once the top was rebuilt, flashed properly, and I always pour a 4" concrete crown, mortar crowns are a common culprit.
 
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