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If you finger wasn’t in the way, you would see the discoloured area beside the unused bolt hole on the pump. I hope you bought a hold down for that extra hole. Yours was pulled up from the pump. That movement is what accelerates the wear on the O-ring and the leakage. As for your leak, did you push the oil pan back so it’s touching the transmission before tightening the pan bolts? If it wasn’t, the timing cover won’t be flat on the block. If the shop did all this, they can fix it for free
No, the leak is likely at the front. If the oil pan is not touching the transmission the pan may hold the timing cover forward, enough to cause a leak. You can test it and see if you can slide anything between the oil pan and the trans. If they are touching, it’s not the problem. As for the pick up. Yours was like this. The oil pick up tube will move and that gap will open and close. That accelerates the O-ring to wear out. There are three different styles of retainers to fix this. They all have the exact same result. You need one.

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For the record, I'm not directly disagreeing with you. I'm just reminded about my thoughts on the infamous O-ring failures. First of all, that picture with the bent tube is likely on purpose or exaggerated. I've had numerous Vortec/ LS engines apart and they are never visibly bent like that. Second, I don't believe the single bolt retention is the cause of any of the failures. The way I tend to think about it is: every single O-ring that has failed is always hard and brittle but flattened equally all around, not lop-sided like the one-bolt clamping would suggest. There are many O-ring seals in the engine that are similar in design, but don't suffer leaks and failures like the pump o-ring. On the engine: the steam ports, crank sensor, cam sensor just of the top of my head all use a single bolt on a flange to retain the item in place, but they don't randomly spring a leak routinely.

I don't think the pickup tube can wobble either, because its bolted in 2-3 places (depending on if its car or truck) which holds it very firmly in place. Again, just my $.02 thoughts on the subject.
 

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I don't know who Carl is but if you're alluding to me, I need to reiterate that the point I was making was my suspicions with the pickup tube mounting isn't the cause of the oring itself leaking. 100% the oring fails on lots of engines causing engine failure; no doubt there. I was merely positing that maybe it fails due to age and mileage, and sometimes install error/ defects.
 
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