So I am taking the bird out for the first time this season and have noticed an issue with oil drips. I thought perhaps I just needed to tighten the oil filter so I did that last week and did notice any drips after that.

I started the bird today to drive it back into the garage and noticed that it is dripping again. Looks to be just a few drops at a time but it is consistently frequent when it drips.

Any idea what this might be? I tried getting under it last week but only noticed oil coming from the oil filter. Perhaps it is something with the gasket and the seal isn't quite right?

Oil filter, drain plug or rear main seal....an old time once told me, "if your pontiac ain't leaking, then you're out of oil"

They have new Viton seals that solve the issue, but you have to pull the motor to do it right.

>an old time once told me, "if your pontiac ain't leaking, then you're out of oil" <

Must not known a lot about Pontiacs, the driest v8's ever made. Mine doesn't leak a single drop.

If the filter is leaking, it could be too tight, distorting the o-ring. Start with a new filter, tighten by hand until it bottoms, then snug 1/4 to 3/8 turn.

Pontiacs don't leak oil. They mark their territory.

Do you have an aftermarket Oil pressure gauge that's hooked into the top of the oil filter? I had that leaking once.
I also had a bad oil pan gasket that was leaking right by the rear main seal. It would only leak when I was full on oil, once it leaked about a quart out, it was fine.

I bought a new single piece gasket from BOP Engineering and it doesn't leak a drop. Single piece gasket

Did you change the oil filter yourself and did you coat the rubber ring at the top of the filter with oil first? Besides the "put a couple of quarts in the torque converter" we have talked about in the past couple of weeks, the "oil the top of the new filter" is a garage trick that always needs to be done.

There is also the paper gasket between the oil filter housing and the block that can leak.

And X2 on the BOP 1 piece steel reinforced pan gasket. My new 455 had a lot of crankcase pressure until the rings seated and it blew the rear piece of the OEM style 4 section pan gasket out. The new BOP gasket took care of that (and the miles to get the rings seated).

When you change out your oil filter make sure the old gasket did not stick to the block. Ending up with two gaskets will leak.
Cal

Another thing to look at is are you sure it's the filter? If you valve cover is leaking on the rear corner that's exactly where it will run down to. Very hard to see.

did you by chance buy new valve covers?
when I changed my valve covers a few years back...I had drips...found out that 'grooves' in the aluminum covers from the factory or manufacturer , did not seal up with the gaskets...had to add a second gasket , problem solved...

The other thing that can leak is the sender, which drips onto the top of the oil filter

"Did you change the oil filter yourself and did you coat the rubber ring at the top of the filter with oil first? Besides the "put a couple of quarts in the torque converter" we have talked about in the past couple of weeks, the "oil the top of the new filter" is a garage trick that always needs to be done."

I think this may be the first thing my dad taught me in his shop when I was about 12 years old...LOL.

"Do you have an aftermarket Oil pressure gauge that's hooked into the top of the oil filter? I had that leaking once."
Ditto on that one!