Oil Cooler gaskets/ O rings

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I think you need to get the bolt tight enough such that the crush/sealing washer on the outboard side will seal. From the picture posted above it looks like the o-ring on the inboard side is supported by the o-ring gland so it can't be over compressed. You can probably do a google search for bajno bolt torque for the appropriate size bolt/washer.

Edit: I couldn't really find an appropriate specification using google. I think the oil side of the oil cooler is not under pressure. This crush washer seal would be similar to the seals for fill and drain plugs on the transfer case. I found the thread below providing some torque spec for those.

Toyota doesn't give any of these torques in the 60 series manuals.

But if a leak was to exist it would be Oil from the banjo bolt right?
 
One other question I had was when I drain the coolant, I will also drain the block. I have done this before, but I can't recall. The block drain, you just take the bolt furthest from the block (if that makes sense). Not removing it from the block it self. Then slip a hose over it for a clean drain. What size is the hose to slip over that bolt. Is that the proper steps?
 
But if a leak was to exist it would be Oil from the banjo bolt right?
I'm not sure I quite understand your question. If you have oil leaking from the oil filter most likely it would either be from one of the o-ring seals (inboard) or one of the crush washers (outboard). Both of these are secured by the banjo bolt. The mating surfaces need to be clean and flat/smooth, including underside of the head of the banjo bolt (where the crush washer contacts). Having the banjo bolt itself leak (ie. oil leaking through a hole in the banjo bolt) is unlikeley.

If you do see some leaking past these seals, I think the first response would be to tighten the banjo bolt(s). If the leak is from the inboard o-ring and the cooler is already bottomed out against the block, this may not help...
 
The oiler cooler thing is a pretty simple deal OP. Taking nothing away from previous replies from others here, no need to over-think this. Correct O-rings in, washer gaskets in and don't crossthread the bolts and you shouldn't have any issues. Its designed to work this way. Make sure the mating surfaces are clean as stated above. I did this with mine in about an hour including painting and cleaning it up (paint drying time was extra). Not much to this bit. Understand you are trying to do your best to do this right but you can get into analysis paralysis with trying to think too much about it. I am certainly guilty of this. Be careful and take your time. If you have the right parts you will be fine and no leaks. GL and HTH.
 
The oiler cooler thing is a pretty simple deal OP. Taking nothing away from previous replies from others here, no need to over-think this. Correct O-rings in, washer gaskets in and don't crossthread the bolts and you shouldn't have any issues. Its designed to work this way. Make sure the mating surfaces are clean as stated above. I did this with mine in about an hour including painting and cleaning it up (paint drying time was extra). Not much to this bit. Understand you are trying to do your best to do this right but you can get into analysis paralysis with trying to think too much about it. I am certainly guilty of this. Be careful and take your time. If you have the right parts you will be fine and no leaks. GL and HTH.
x2 on this. No need to overthink this process. Just make sure everything's clean, don't overtorque the banjo bolts, use new O-rings and seals, and one thing that I didn't see mentioned in this thread: lubricate the O-rings with oil when you install. It helps them seal better in the long term and last longer.
 
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