1996 Chevy c1500 leaking and dropping 10 mm bolts

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sewlow

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Erik the Awful

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Pic #1, that's a droplet of oil collecting under your drain plug. Might be oil pan bolts, might be the drain plug
Pic #2, that's coolant droplets hanging off your transmission cooler lines
Pics #3 & #5 lead me to believe your crank seal is leaking

You have more than one issue.
 

victor II

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In my experience gaskets collapse over time. Lock washers break too. I replaced all of my oil pan, trans pan and rear end cover bolts with new grade 8 stuff several years ago when one snapped. I also go under the truck now and then with a 1/4” drive socket set and rag and wipe where necessary and snug ‘em up. I have a little drip here and there but not bad for an ‘88 that’s never been apart. Also check the oil pan drain bolt. I use the neoprene/metal washer gasket and it’s good to snug that up too. My 2 cents.
 
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