Paint chimney before re-covering with new wainscoting?

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May 19, 2024
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Roof was replaced, but before that it leaked. I'm not entirely sure if it stopped leaking. It seems to have stopped.
How many moisture events since the repair?
What was the extent of the repair?
Do you have, or can you post photos of the area of the roof penetration and the repaired area?
70% sure the leak has stopped.

I just got this house so I don't know for sure, but the tenant (it was a rental) vaguely seemed to say the leak has stopped. I can call the previous owner to see when they put the roof on. There is wood rot up in the attic above this spot. I'm fairly certain the roof was leaking and then they put the metal roof on themselves, not remediating the wood rot.
If the water from the exterior is stopped & you want to cover the bricks with something to keep interior moisture & humidity from getting into the bricks, a product such as Mapei Aquadefense & Custom Building Product's Red Guard are suitable on clean and dust-free bricks & mortar.

I like Aquadefense because it is very low VOC. Note that neither are very paintable, so you'll have to go back to wainscotting or perhaps tile the chimney. (Or thin bricks on the coating.)

I already have

Zinsser® FastPrime® 2+ Multi-Purpose Sealer & Primer - 5 gal.​

and it says it seals masonry. Thanks everyone for your help.
If it's not too late, a good test to find if water is still entering is the tape a piece of plastic wrap or other clear plastic over suspect areas. Tape the entire perimeter. After a rain, check the plastic. No droplets? Yay! (Also wait a day for soaking through time and re-check.)

It also may help to install a rain cap on the chimney if it's got sectional flue liners inside. Water gets through the joints in the liner sections, wraps around the edges and goes to the bricks.

Best of luck with this challenging project. It sounds like you're on the way to success!