Help! - Leaking windows. Seeking ideas and potential contractor

[Blair Nye]

Two southwest facing windows in the top unit of my duplex are leaking water whenever it rains hard. There is no obvious ceiling / wall damage. I have inspected from inside the attic just above the windows and can’t find the source of the leak. My handyman caulked the exterior all around the windows and water is still coming in. 

Any ideas what could be causing the leak? 

Any contractor recommendations? 

Any help is greatly appreciated.

[Will Fraser]

HI @Blair Nye!  This recently happened with my personal home with brand new windows!  Knowing the common mistakes that installers make in water defense (thanks to Matt Risingner on The Build Show) I poked about a bit and found that water was getting behind the wood siding boards in an area of wood rot well above the window.  Water was traveling down wall behind the wood siding and coming out through the screw holes in the window frame.  The issue was remedied by sealing off the areas of wood rot and re-working the guttering to be more effective.

A general handyman could get the job done with some good guidance, or any excellent window installer should be able to pinpoint it.

In general, remember the adage:  "down and out"  That's how you should move water away from the home and any violation of that will wreak havoc on you in the long run.