Oil leak from the back of the head.

1989 B2200 with less than 600 miles on a full rebuild. Re-torqued the head bolts a week ago and found fresh oil underneath the fuel pump. After closer inspection it was not the fuel pump but it was coming from where the head gasket is on the rear of the engine. Decided to pull the head and make sure the head gasket wasn't crap and this is what I found. That is the elongated dowel pin hole on the rear of the head gasket where the leak had been found. The cylinder head also had oil on the rear freeze plug. The cam seal and valve cover gasket were dry. I checked the head with a straightedge and all is well on that part. i did use a FelPro head gasket set as well as made sure all gasket surfaces were clean and dry. Being that there was oil pooled on the rear freeze plug is it possible that the head could be trash? I have no oil in the coolant or coolant in the oil, all pressures are normal with the engine. So anyone have any ideas on what it could be?

How does the silicone seal look around the oil drain back hole... Just to the left and down from the dowel hole?

It was still intact but when I went to clean the head gasket off with a shop rag the silicone rubbed off some.

Was the head resurfaced? Pressure tested / checked for cracks?

It does look like you put the gasket on dry (which some recommend) but I always use red spray hi-tack.

Were the head bolts new and did you lube them at least with oil?

Yes the head was resurfaced and pressure tested. I have always installed head gaskets dry. It was the second run with those bolts and they were lubed with oil. I have a new set of head bolts now, had to wait for them to ship due to the holidays. I have a bad feeling that my torque wrench may be faulty, it's an old Snapon that has seen a lot of use and has been dropped a few times.

Sounds like you did everything right - what did you do to prep the block?

You should be able to calibrate the TQ wrench on any snap-on truck.

It does look like that one head bolt was maybe over torqued.

I used a thread chaser for the head bolts and blew out whatever debris was in there with the air compressor. The block had just come from the shop so all I did to prep the gasket surface was spray carb cleaner on a shop rag and wiped off the machine oil they left behind. Bad thing is the Snap on truck doesn't come out this way anymore. The shop it used to go to changed their tool company recently. I am going to find a local Snap on distributor and take it to them and have it calibrated.

Yeah, the more I look at that picture, the more I think the one bolt got way over torqued.

I would also use brake clean and not carb cleaner as the carb cleaner sometimes has lube in it.

Hope it works second time around!

Be sure to check the head to make sure it's still straight.

I agree, it is really easy to see going by the impressions left on the head gasket in that area. When I removed the gasket I noticed a oily film on the gasket so it's brake cleaner from now on. Turns out both of the alignment pins in the block had burrs on the outside edges also, so I sanded them down to where they are smooth. The holes in the head showed where the pins had gouged into the metal. Also my torque wrench is almost 15 lbs off, I was able to test it against a friends Snap on digital torque wrench. 15 lbs off can kill a head gasket in a hurry. I will post my results once we get some warmer weather here, my shop has no heater right now and here in northern Louisiana we tend to stay inside when temps go into the teens. Thanks for your help on this.

I'm just throwing this out there, take it for what it's worth...

Did you check to see if you have a crack in your fuel pump plastic spacer? I've chased a similar oil leak and it turned out to be a hairline crack in the bottom of the plastic spacer.