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About 5 years ago I noticed the paint chipping on the ceiling around the chimney that vent my furnace and water heater so I hired a guy to replace the flashing around the chimney.

Since then I've noticed further damage and paint peeling in the same area, so I went up in the attic and monitored the roof during 2 rain storms. I observed no water leaks and the chimney, sheathing, and tar paper around the chimney were bone dry.

I also looked for leaks along any of the sheathing and observed no leaks.

I'm very stumped as to what is happening.

Some background information on the house:

-Built 1930 -No insulation around the brick chimney -Chimney liner is original as far as I know -Area below the damaged ceiling is a stove with no range hood

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As much as you may want to avoid it, the best way to find the source of the water leak is to open up the ceiling and trace the path back to the source. Water can run a long way across ceilings, joists, roofs, etc. So if the non-destructive investigations didn't reveal anything, it's time to do some investigative demolition. You'll also want to leave it open until you see the leak happen again and then wait until the fix it tested before closing it back up. The only positive in this is that you really should remove and replace the moldy parts of the wall anyway, so this is positive motivation to fix it right.

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The leak could be in the chimney itself (rain comes down the chimney and seeps through.

Also, you mentioned no insulation around the chimney, but maybe condensation is dripping from inside the attic.

If you lay down some newspaper above that spot in the attic (a few sheets, dry), and then check on them every few days through a rainstorm or two, you should be able to see if the water is dripping from above or seeping horizontally.

Water is notorious for seeping along seams and cracks so that water damage is far from the source.

  • We used to have chimneys where rain ran down the inside. We got little steel rain hats made for them and that did the trick. If you Google "Kamin Hut" you can see lots of different possibilities. – RedSonja Oct 30 '15 at 12:03
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If there's a stove directly underneath the area in the pictures without adequate ventilation, this could also be due to steam and heat coming from using the stove.

From the look of the old paint and plaster underneath the peeling paint and wallpaper, it also looks like this could be exacerbated by inadequate prep work before it was painted/wallpapered. That, combined with the heat and steam from the stove could easily cause the finish to start peeling off. Once it starts peeling, it generally goes downhill from there.

One option to explore would be installing either a range hood or an exhaust fan - although if you're refinishing the area anyway, just doing a better job of prepping for paint than the last guy will go a long way if you're not getting any indications of water ingress.

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