Troubleshooting air leak near the head with bonus: cylinder stud pulled out

[2017FLHTK]

Dude.... something is very wrong here. Are you 100% sure you have the gaskets oriented correctly? I just looked at my '92. The MLS head gaskets have the rivets on the left/right side of the cylinders. In your pictures, they appear to be pointed to the front/rear.

I would call James Gaskets and talk to them about this. They make thousands of these, I can't imagine the problem is with the design of the gasket.

-JW

I feel pretty damn confident that I had the James gaskets correctly oriented.  Because the gasket indexes off both the cylinder studs and the dowels, it's not possible to incorrectly install them rotated 180 degrees out of phase. The instructions provided by James don't even mention the rivet, and certainly don't mention one side or the other being needed to be "up" vs the other side.  I took the head off today and saw no indication that the gasket had moved or slipped; they were locked in place on the cylinder dowels and appropriately posistioned.

As a hail Mary, I went to the dealership and picked up an OEM HD head gasket (part number 16770-84F).  Side note: my factory service manual has a caution that states "Install new O-rings over the cylinder dowels before installing the head gasket.  Install the O-rings first to ensure alignment of the head gasket and prevent gasket leaks".  I didn't catch that until I was back at the house with my new HD gasket in hand, so I went back to buy the O-Rings (HD part number 26432-76A).  However, with the O-Rings in place my HD gasket would NOT fit flush with the surface of the heads.  As it turns out the MoCo has changed the construction of their evo head gaskets (as compared to what was in use from the early 90s), and now are designed to be used without the cylinder stud O-rings referenced in my older service manual. 

Good news: with the OEM gasket installed and torqued down to the specs in the service manual the head seams to have sealed up!  With my leakdown tester installed I was able to pump in 100 PSI of air on the supply side, with 92 PSI indicated on the cylinder gauge!

Unfortunately I got called out of town on a work trip, so I didn't have time to perform a leakdown test on the other cylinder, but I feel confident that I'm headed in the right direction.