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House is 10 years old and has recently started to leak under this bump out. I'm going to replace the roofing here (3'x12') but I'm not sure what to do with the flashing at the headwall. It is nailed through the top of the shingles (no sealant over the nails however) and tacked to the wall. There is sealant at the top of the flashing but there is no counterflashing. I believe this is where the leak is.

I've been looking around my area and it seems this is the typical way this joint is flashed. I guess my options are to 1) replace the sealant, 2) remove and embed new flashing in sealant against the wall, or 3) cut a groove and install counterflashing.

What would you recommend here? Appreciate your advice.
4235
 

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I'd install new flashing, with the wall leg of it tall enough to meet that brick joint above the current. Using hand tongs, bend the top over by 1/8th in to fit into the joint. A siding company should be able to fab the new for you from left over coil in a color that complements the shingles. And welcome to the forum!
 

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cutting into the mortar line or properly installing a surface-mount CF wouldn't be difficult.
Never rely on caulk or liquids as your primary waterproofing. It always fails loooong before all the other components.
Nothing else I see in that picture seems to be problematic other than the exposed nails at the base of the flashing but they are not causing your leak.
 
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