Leaking Chimney

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We bought a house that now has a leaky chimney/chimney area.

The water doesn't come in as soon as it starts raining, but after some time goes by and the rain continues.

The way our chimney was constructed is that it is actually wider at roof level and higher and comes in on an angle on the one side that leaks once inside the attic. It comes in about one 1/2 brick per brick level, almost like steps ( upside down ) because the bricks farther out extend over the next lower level down as the chimney becomes skinnier.

We first see water dripping from the bricks. It isn't getting the wood wet. That is until it drips so much their must be back up of water and then the lower side of the chimney starts to leak on the wood beams.

Do you think the water is coming through the brick or mortar? I have been up on the roof many times. And I see nothing. We have had a roofer redo the flashing twice and the problem has never been solved. He has even used what he calls "blackjack" as the sealer for the flashing. He said that when he used the regular flashing sealant, when he came back the second time, it peeled right off and was wet on the back side of the sealant. This sealant is the sealant at the top of the flashing where the flashing meets the brick.

Should I use more sealant?

Should I use a water repellent treatment like Thompson's ?

Please help. Winter is coming soon and I need to get this fixed.

Thanks very much for your help.

John Fitzgerald
fitzrr@msn.com