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Mystery Window Leak—Jamb

My project was to insulate the window boxes. Three windows together. When I removed the trim of the jamb and head I found soft wet wood at the bottom of one of the window boxes (the three others were dry). The soft, wet wood has been removed leaving a hole in the bottom corner of jamb/sill approx. 5" square. The stability of the window is not compromised. The leak was detected and deemed responsible for the rotting. But now we can not find the leak source. We had the exterior top of the windows recapped and everything on that side of the exterior has been recaulked. We must have recaulked about 5 times now with everything from silicon to Dynaflex to Quad. Luckily the home is brick, so the water from the leak puddles on the cement frame. Sticking my hand in the hole when it leaks, I feel the jamb wood behind the window box back is wet. But we can not determine how it is getting wet. We’ve examined the roof it is intact. We have a flat roof, tilted to the back of the home and the leaking windows are in the front.
Frustration has set in. Any advice would be appreciated.

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