Water is coming from above the window in this case. We need to see a picture of the exterior of the home.

We need to see the flashing that is "done correctly" please.

It’s the bottom left windows (the 3 in a row). The one next to the sliding door leaks the most.

Come on Gatlin,the guys are trying to help you. Why can't you help them to help you?

The upper 1/4th top of window where it meet's siding has to fill picture and another of other corner of offending window would also be good.

Can we get some close ups of the areas indicated in this picture. From the top down ideally.

The contractor that came to look at it added more flashing. It was leaking prior and after his fix.

Okay, thank you! Once I figure out how to remove I will post more pictures. I appreciate the help so far!

Properly installed vinyl siding is easy to unzip. It isn't nailed tightly to allow for expansion and contraction. Grab the siding, feel for where the nails are, and pop it off the nail. Goes back on the same way.

Don't forget the flashing picture please.

ln your last picture, I can't tell if that's a gap between siding pieces or a shadow. If it's a gap, there's yer problem.

Look here please.

There is a hard ”bump” on wall above corner. Not sure if I should further investigate. Bump is shown below in picture between fingers.

That is a poor flashing job. Fire the "contractor" that said it was please. Your installation looks nothing like pages 24 and 25 of my previous link. Flashing doesn't attempt to go over the top of window casing as yours apparently does.

On a dry day, take a hose, squirt it 10' above the window so you'll know the window itself isn't leaking, let it trickle down, and watch the water pour into the house. No need to rehang the siding for the test. A properly flashed window won't leak with no siding applied.

At five years old, you've got some rot and/or bug infestation. Looks like I'm seeing frass already. Reinstall the window properly please. And all the others probably too.

Thanks Joseph. Are you thinking the water is coming in because the window is installed incorrectly?

I see goop where there should be flashing but I don't see anything that look's like flashing. Joseph is right,all the calk and silicone in the world can't replace flashing. Or more accurately,properly installed flashing.

To witness just how well flashing works,look at shelters made from plant parts in third world countries. From inside those huts you can see the stars but when it rain's the inside stays dry. To prevent leaks,follow the same principle when roofing and installing flashing.

Should the missing flashing at the top be a drip cap?

A drip cap and flashing are two entirely different thing. You need someone to come, remove your window, inspect for damage and rot (and there probably is by some), repair it all, reinstall the window, and do the flashing correctly. Once that is done, if you want a drip cap too, ask for one. It will do nothing for that window right now anyway. Some siding will have to be removed for all this and then reinstalled. Ask the person you interview for this job, how they do the flashing (before this look it all up, so you know how it should be done), and then watch when they are working, to make sure it is all done correctly.

"Are you thinking the water is coming in because the window is installed incorrectly?"

In the sense that the flashing is laughable, yes, the window is installed incorrectly. It's a do-over. As in pull the window, repair, reinstall, do-over. I doubt this installation is a one-off. I'll bet the rest, and the doors, are as poorly done.

And no kiddin' around. This is on the way to being something very serious.

Yep,and in this case serious could mean expensive. You might try researching history of that siding and see if a warranty is in effect.

Thank you everyone for your help, knowledge and quick responses. I am looking into local contractors for quotes.

Please look up window flashing for windows, so you know exactly what should be done, and keep an eye on the contractor to make sure its done properly, so that this time its right. Hopefully, once he removes the siding and the window, you wont find a lot of rot and mold in that area, since that could get very expensive.