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Two questions (usually not a good idea since one question usually gets ignored but here goes):
1. Should new head bolts be lightly oiled before torquing or go in dry?
2. For torquing other components where you can't physically get a torque wrench on some or all of the bolts, what do you do in this case if there are multiple bolts and an even torque is needed (e.g., gaskets for hard to reach parts)?
 
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To get the most accurate measurement, bolts should be oiled. However, I usually do not. What I typically use is a thread locker. The liquid form will benefit the torque reading like oil, but will provide a measure of added safety. And in regards to headbolts, you must keep some of them sealed from the water passages. So a sealer is needed.

As for other bolts and nuts around the car . everything when designed and engineered will have a torque rating. And on paper, all is well. But in reality, there are components that don't need that amount of exactness. So . . this is very personal and not scientific, but I know about how much torque I provide with a wrench or ratchet. I'm sure most don't test this and I haven't retested myself for a change in age LOL But I have a "feel" for how much torque I apply with a given wrench. I know what 25 lbs feels like with a 1/2" wrench as well as what 70 lbs feels like with a breaker bar. It works. But I try and use a torque wrench when it is needed. Understand that any change you make, extensions, etc, will effect the final outcome.
 

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Yes, oil will help get a good healthy torque reading. Head bolt holes need to be cleaned out so oil does not squish out onto the gasket. Threads should be clean with maybe a minute amount of oil. Torque the hard to get to bolt to the same feel as the measured torque bolts. Use the same wrench on both, after the easy one is measured with the special wrench.
 

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Oiled will yield the most accurate preload and stretch on the fastener. Proper method is to lubricate the threads AND the head of the bolt. Where sealant is required, seal the threads and apply oil to the head prior to installation.
 

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critical bolts on ALL cars from the 60's and 70's used 30w oil on the threads and the torque specs given are for oiled bolts. all the critical bolts on my 2006 F350 are to have the threads oiled for accurate torque readings. as the bolt/nut tightens the oil allows the threads to move freely against each other. dry threads produce friction and do not give an accurate torque reading and can also damage the threads especially grade 8 bolts against cast iron threads.
 

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Yes, use oil. On a side note, dirty/rusty/greasy galled threads will prevent accurate torque. Use a bottom tap to clean the block threads and blow them out good with solvent.
 
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