I just had a new roof installed with new chimney flashing 8 weeks ago. We’ve had some fairly long hard rains and I didn’t notice any problems. Yesterday we had very hard wind driven rain for about 10 hours straight and I noticed some water coming in on the corners of the chimney on the side that was getting pounded. The flashing looks to be fine with no glaring defects. The chimney is 50 years old and was pointed 9 years ago, is it possible that the rain could be coming through the brick or the mortar joints? Thanks. -Ed
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Anything's possible with wind-driven rain. But if it didn't leak before this you should at least ask the roofer back to check it over.