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I'm in the process of replacing the heads on my 351w (the left one was cracked). While I was removing the right head one of the head bolts was covered in oil. And it smelled like the oil had been over heated. If you know what I mean. Is there a oil passage that or something that the bolt goes into inside the block? And it's the second bolt from the back along the valves
 

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No explanation for the one head bolt having oil. Likely, cooling system was failing on the right head causing oil to burn. To my knowledge, bolts are not used on any motor as part of the lubrication system; push rods, rockers and heads have oil passages but not bolts.
 

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If I understand, it's the bolt under the valve cover (?).
If that's the case, it might be the rocker arm next to it squirting oil outside of the rocker arm. I've seen them squirt in some pretty random patterns, especially when they get dirty.

Head bolts are solid. As TomR described, valve train is lubed via lifters, pushrods, and onto rockers.
 

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I don't see how that would cause oil to get down into where the bolt goes into the block
It wouldn't. I misunderstood your description. I thought it was on the head of the head bolt. :doh0715:

IIRC, those are blind holes. About the only way that could happen is a blown head gasket, a cracked head or worse car scenario, a cracked block.
 

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A cracked block was the first thing that came to mind but I tried to box that thought up and store it in a deep dark corner in the back of my mind. I inspected the head meticulously where the bolt runs through the head and no crack was found
 

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Don't blame you. Just had a similar "scare" on my 7.3 diesel. Luckily it was the gasket.
Be thankful your heads don't weigh 100 lbs each.

I am not all that familiar with the oil passage routes in a 5.8 block. Seems extreme that a block would crack between a head bolt cavity and an oil passage. The only thing that bothers me about thinking it's a blown head gasket is where all the oil would come from. The oil comes out of the rockers and gravity drains to the corners of the heads and drains into the pan. It's getting late for my brain, maybe I'm missing something.
 

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Luckily it was the gasket.
Be thankful your heads don't weigh 100 lbs each.
Wouldn't matter it's sitting under an A-frame with chain falls that are used for pulling tractor engines Haha.

But I'm pretty stumped, I would just like to find out what's going on before I put the new heads on
 

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Wouldn't matter it's sitting under an A-frame with chain falls that are used for pulling tractor engines Haha.

But I'm pretty stumped, I would just like to find out what's going on before I put the new heads on
I used a cherry picker, my back doesn't tolerate this crap much.

Did you run compression tests before you pulled it down?
 

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May not be the first time the heads were off, and the last guy oiled the bolts before install. Pretty common practice.
 

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May not be the first time the heads were off, and the last guy oiled the bolts before install. Pretty common practice.
It's definitely not the first time they were off; noticed by the incredibly bad valve job. However it's just one bolt that has oil on it and it's covered with it. Not like it would have oil on it from installation. Also it wouldn't explain why the oil smells over heated
 

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That's odd, only one bolt.
 

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That would concern me then (the bad valve job and the oil). That would make me consider that they didn't prep the block well before re-installing heads. Most recommend cleaning the threads and making sure no debris or oil/water remain.

If they cracked the block in the bolt hole it would probably be hard to see with the naked eye. A borescope might help to inspect after you suction out the oil.

I think I would make a "test" tool to pressurize the bolt hole. I don't think I have ever seen a commercially available tool.
I'd use a soft (grade 2) bolt & drill a hole (maybe 1/8") from the head to the end of the bolt. Drill and tap the head for an air fitting for compressed air. You could also weld a steel fitting to the head. Use thread sealer and thread the tool into the cleaned out hole. Apply air and see what happens.
 

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It's definitely not the first time they were off; noticed by the incredibly bad valve job. However it's just one bolt that has oil on it and it's covered with it. Not like it would have oil on it from installation. Also it wouldn't explain why the oil smells over heated
I don't think there is enough "room" in the bottom of the hole to accommodate the bolt and a bunch of left over oil/liguid as you describe. Compressing any liquid in a blind hole would be risky. If they were that crappy of mechanics they could have installed it with an impact and done some damage.
 
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