Yeah, a little more info usually helps, but I'll offer this...
If this is a high mile motor, you may have excessive crankcase blowby. If this is the case, maybe the point where it leaks is the weakest link. In some cases, a worn out engine will push the dipstick out of the tube and spray oil and crankcase vapors out.
Big blocks have bolts at the entire perimeter of the oil pan. I have no memory of having any leaks in the 5 440 engines I have had at the area you mentioned.
Small blocks have the half round rubber seal. If the oil pan has stayed in place while the timing cover has been off before, the front 1 1/2" of the oil pan and gasket is vulnerable to tearing. Most Timing gasket sets have small sections to replace these exposed oil pan sections. If this is the case with your app and you DON'T have a blow by issue, maybe you could pull the pan and replace the entire oil pan gasket set .