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Chris, I'd also recommend filming your oil filter bowl O-ring with vaseline as Woody mentioned.

On airline jets it is not a "trick" but standard procedure to lube O-rings that go on the oil system drain plugs and filter bowls with petrolatum (purified vaseline) to prevent twisting, bunching, rolling, cuts, etc, during installation.

Don't gob on too much. Just a good film should be enough to keep it from bunching up. Perhaps also smear a slight film on the engine block where the filter bowl's O-ring mates up, below the bowl threads.

Nonetheless, I was studying the picture you attached and think it looks strange that there's a section of casting that is raised on the perimeter of where the filter bowl O-ring chamfer is. Maybe one of the other guys on this forum can see if they have the same thing when they do their next oil change.

Good luck.