Siding leaks!

I have cedar siding on my house. The panels have overlapping vertical seams, and look like they are made up of several thinner pieces. Sorry, don't know what they are properly called.
Where the deck is attached to the house, I have had rain come in through the siding and run down the wall of my walk-in basement. I presume the wind blows the rain againt the house; it cannot run off and must go somewhere, so it goes through the siding.
This has only happened twice in the 13 years I have owned the house, but it still annoying. I am having my house painted by someone who is also a carpenter, so I had him look at it.
He says they should have put flashing in, but there is no way to do that now. He thinks caulking it will probably just make it worse; so his advice is to clean it out as thoroughly as possible so the water can run through rather then being forced in, and then just live with it.
Any suggestions?
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Toller said: He says they should have put flashing in, but there is no way to do that now. He thinks caulking it will probably just make it worse; so his advice is to clean it out as thoroughly as possible so the water can run through rather then being forced in, and then just live with it. It can be done, Toller. This is mostly moot if you've got the pre-fab cedar shingle siding, and it's kind of involved. Remove the deck boards so you can get to the ledger board on the house. You'll need a tool to slip up under the cedar and hook onto the nails."Slate puller". This tool also has a surface to whack with a hammer. Have at it. When you're about three courses up from the ledger board, you install a "z-strip" flashing over the ledger and against the wall sheathing. I'd tack some 30 lb. felt over the top of the z-strip and under the bottom course of the shingles, up as far as possible. Snap a line to get a nice straight starter course of cedar, using pieces about 2/3rds long, the butt end cut away.(Snap another line above that, that corresponds to your exposure to the weather) Overlay another course of full shingles on the first chalkline, offset at least an inch or better from the starter "keys"(the slot 'twixt the shingles). Keep going up, being careful not to overlap any keys. Nor should 2 keys line up even when they're 2 couses apart (in case the middle one splits). That, or hire a good roofer. I've retired. Tom
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The correct way is to install flashing but my moron builder did not and when I had a leak he caulked it which stopped it for several years. Also caulk aroung the bolt holes that connect the deck to the house. It will last a while... perhaps until your deck needs renovation.

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