I have been battling a significant oil pan leak on my 383 RR that has been driving me nuts. It always leaks from the same areas - the two front corners of the pan between the gasket and the timing cover bottom flange. It does not appear to be leaking from the sides of the timing cover where it mounts against the block, at least I can't see of feel any leaks.
I have tried two different pans, one was a used OEM pan and another was brand new aftermarket. I have tried it without any sealer or RTV and the last time I used a thin layer of Right Stuff between the gasket and the pan, but not between the gasket and the block. I have used both cork and the crush proof Milodon gasket, both leak in the same spots.

I'm thinking the only thing left to try is a new timing cover?
The timing cover flange appears flat with no issues, however, I did notice the last time I bolted it up is that one of the front bolts that screw into the timing cover flange goes in at an angle. In fact the old pan that I took of this engine had the front bolt holes elongated which I thought was strange. The bolt hole on the timing cover is not cross-threaded, it just appears to be drilled and tapped at an angle. The bolt goes in but the complete diameter of the washer and bolt does not sit flush against the pain rail. It cinches down at an angle.

I'm thinking this could be my issue? However I don't know why it would leak at both corners. The other bolt that goes into the bottom of the timing cover goes in straight. Otherwise I don't know what else to try next. I don't relish the thought of tearing it down to get the timing cover off - think chipped paint. But I want to get past this hurdle. The summer is slipping by.

Any thoughts? Thanks!

Thoughts? Yea, are you 100% certain its not the crank seal? They can be deceptive.

I bet it is the TC. I had what I thought was an oil pan leak a few years ago. I tried everything, new gaskets, sealant torqued the bolts. The problem was the the TC had separated on the bottom where the stiffener is. I changed the cover, no more leak.

Can't feel any oil underneath the crank on the front of the cover nor any oil on the top of the timing cover flange.

I bought one of AndyF's billet TC covers and one of those new $60, one piece, metal insert over silicone pan gaskets. THAT elimiates any leaks. I hate oil leaks!