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Two questions.

1) How imperative is it to have new copper crush washers or have them surgically clean? I cleaned all of them off, but I have an oil like at the oil filter connection.

2) How tight should these be? I had a coolant leak near the AC compressor, I tightened the bolt (though it was already very tight) and that cleared up, but I don't want to strip or over tighten the oil filter connection. I cleaned the washers before I put them in, but I'm wondering if a spec of dust will cause an issue (And hence the leak, if that's the case) or should I just tighten it and give it another go? Thanks TSL community.
 

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You should be able to find them much cheaper than that. Try the oil section of an auto parts store, or call around to a couple of different places. A CarQuest near me had the puffy crush washers, which actually do crush when you tighten them, unlike most so-called "crush washers", and they really sealed everything up. I had a couple of little drips before putting them on. I think they might've cost me $2.00 each, which I thought was ridiculous for a washer. Another option is to give them a light sanding to clean the old ones up. I had to do that with some aluminum crush washers that came with a pair of Earl's banjo bolts.
 
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