After another long rain from a tropical depression, the ceiling near the chimney is leaking again, what to do?

I had the homeowner's assoc. fix the problem the first time. Then they re-roofed, but now the problem seems to be the chimney and its failure to seal out water. The HOA wants to repair the ceiling again but did not mention solutions to the chimney this time, should I agree with their offer to just repair the ceiling? Or should I taken more action? Repairing the ceiling every time this occurs is not a good solution, but I'm not an expert here about what to do. Any ideas for me, anyone? Thanks.

Answer:
go to your local hardware store and buy yourself a gallon of roof sealer [plastic] trowel grade and a i inch trowel. the go up there and go all around the chimney with a neat strip, making sure to fill the open tin spaces. alot of roofers just use tin flashing and it really has to be tight for a hard rain. unfortunately it seldom is tight. pay special attention to the uphill side.
somebody needs to put some blackjack (roofing tar/asphalt) around the seam between your shingles and your chimney. after that, you shouldnt have any reason for the ceiling to need replacing.
Have a roofing contractor come in, document the problem and write an estimate, then turn the estimate over to the HOA. They don't have to use the contractor you picked; they probably have their own contractors picked out. But if you have documented proof of the problem, they'll be more likely to act on it. If you fix the drywall without fixing the source of the water leak, you'll just have to have it fixed again in a few months.

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