new headgaskets leaking oil? dowel pins

[Veikra]

Ok, took my oil cooler off to replace oring as I have a large oil leak.

It looks like my headgasket is leaking from the rear corner of the driver side.
The heads where milled and pressure checked.

Could the milling have made it so the dowel pin kept the head from sealing? We cleaned the deck block really good, but did not clean that area as it's unreachable with the cooler there.

Keep in mind I do have a fuel leak from the return lines, so maybe it's washing stuff down the engine. The uppipe has signs of engine oil and when I removed the bolt from the cooler, it had a good coating of engine oil.

Im pretty sure I torqued them all correctly but im doubting everything now

Here's the pictures. Tell me what it looks like

I could try testing the torque on that headbolt near the glowplug.

 

[Veikra]

I have a video , truck ran the day and just parked. I thought it was the oil filter but it's not https://www.youtube.com/watch?v=tYeuGzR3Elc&list=UUisf5I4yhyMJnQ1uBQAY5uQ
The first few seconds you can see the puddle it makes.

 

[DPC]

I would fix your other leaks first, clean the oil and fuel off, and recheck.

 

[Veikra]

Seems thunder550 found the same problem on his truck, the headstud at the back is hiting the valve cover preventing it from sealing. I must have one of those blocks with shallower rear hole.

see:
http://www.duramaxdiesels.com/forum/showthread.php?t=50518

You can see the last picture, the cover isn't sitting on the end . It should be flush and it's not.

I'll take it off and see. And fix the return line as I got another kit in the mail this week to tend to that.