We bought this “awesome” house this year and have had three totally distinct leaks. The shower curb leaked, we got the ac unit serviced knocked out the condensation pipe and a big leak in the ceiling ensued so in my obsession with water management did a full inspection (visual and with a moisture meter) to see if there were any other leaks. 

Found one. Right in the corner of the fire place where it meets the ceiling. We have a bunch of drainage / gutter issues and we had gutter guards and some valley shields installed (which maybe be the cause here). This particular section of the roof / gutters is hectic and without the valley shields yeets water off the side. 

First pic is before any demo. The spot right under the trim was ready 100% wetness. The paint pulled right off in a sheet. 

The second and third show the wet dry wall removed . The insulation was decently dry and the only place I could find actual water wet enough to wet my finger was right on top of the joist? Header? Dont know the right term but maybe a couple inches square but wet. 

Pic 4 / 5 are the outside roof line and eaves. There is a section that runs the length of the house with an eave then the corner runs perpendicular. 

6 and 7 are under the eave and the arrows are based on measuring right on top of the interior wet spot. 

It seems like a new leak based on the amount of water or only got wet because its been crazy rainy lately and overflowed the eaves and gutters a splashed under the eave and got between the siding where there isnt any flashing. 

The last pic shows where the chimney comes out through the roof. It might be here but seems stronger evidence given the other pictured and spot. 

My best guess is that because of how the roof is designed coupled with the gutter guards and valley shields water is getting around the top eave and finding its way to the gap between the house and the lower eave picture 6 and getting behind the siding. Picture 5 shows some water coming down under that eave on the siding and the little corner siding piece looks like its been wet a time or two directly under / adjacent to the wet spot. I cant conceptualize how water would get over there but I think it is.

We think that is what is happening?

It best fix to put some flashing up there and caulk the hell out of it? A roofer is probably going to charge me $600 just to smell it. This a DIY or call a pro situation?

There is also about a 3” insulation gap running vertically right behind the fireplace where it looks like they tried to spray foam but didnt. The wet spot is right at the top of that gap. It could be condensation but id expect water / condensation the whole length and its really just at the top and trickling down. 

HELP! Interior leak coming from roof (I think) so