HJ45 oil in water jacket

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Reposting here in the hope of a wider audience - I posted in the diesel section but tbf I rarely look in there even myself.

Got my engine a bit warm last year because the rad cap was leaking and my gauge wasn't working at the time. It hadn't lost much coolant, so I topped it up with water to limp home.
Forgot all about it and it sat most of the winter. Ran it for a while today on the drive, and I've got steam pouring out of two core plug holes, while 2 core plugs lie on the ground beneath.

No big deal I thought, just replace them.... but then I discover both holes are full of oil too.
No sign of water in the oil, no emulsification on the stick or at the filler.

Ran a compression test and have nearly 400psi on all except pot 5 which is making at least 340psi. Seems OK for a 1977 H motor.

I'm assuming it's broken through the head gasket between oil and water, but happy to hear any other suggestions before I tear it apart (once I track down a mythical head gasket for a H motor that is...).
 
That would be my guess - head gasket. Have you tried to retorque the bolts with say a few extra #.
 
That would be my guess - head gasket. Have you tried to retorque the bolts with say a few extra #.
Haven't even checked the head bolts yet tbh. I guess if they were really loose then I might have confidence in that, but it's hard to determine if oil is still leaking inside.
Hoping that my top end has actually been getting at least some oil recently.
 
Things get longer when heated. Cast iron grows at a different rate than steel bolts. The gasket is designed to work in a heat range for a long time without issues. Exceed the range then all bets are off. It cost nothing to check the torque and maybe add a few % to try for a good seal again.

On the gas I6 cylinder 5 gets toasted from leaking brake booster.
 
I'll definitely give it a try - doesn't cost anything :)
Not enough vacuum on the diesel engine to power the booster, so at least I won't suffer from that. I'm running an electric vacuum pump since the original alternator (with mechanical pump attached) got switched out.
 
So a quick update on my potential head gasket failure..
I removed the rocker cover to re-torque the head bolts, and discovered 5 more blown core plugs that I didn't even know were there in the top face of the head.

I'm hoping (with everything crossed) that these plugs are the only cause of oil in the water.

Waiting for a new set of 24mm plugs now to go with the 28 and 30mm plugs from behind the intake manifold.
 
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