59 Exhaust Flange Leak Issues

My 59 with 352 engine and original exhaust manifolds keeps developing leaks at the exhaust flange. Not at the head mating surface but at the surface where the exhaust pipes attach. New gaskets are a temporary fix and before long I begin to hear that annoying ticking sound under an engine load. My 60's Fords all use a better round donut style gasket, but this 59 had a flat gasket and it just doesn't seem to hold up. My surfaces look good but I keep developing leaks. Any ideas? What do you guys do?

This is a common problem & even though your matting surfaces look good they are probably not matching up perfectly.
I have had this problem in the past on some of my cars and if you don't want a muffler shop make up new header pipes you can cut the pipe in a spot where it is easy to weld in a repair, get a piece of pipe that will slip over your cut pipe and then reinstall.
when you have the header pipe tightened up you can slip the the repair collar over where you cut the pipe and weld in place, you should be able to see how much out of alignment you were by looking at the cut on the pipe.
I have done this on a few cars and have had as much as a 1/2" mismatch in the two pipes after they were cut.
Another repair I've done that seems to work for awhile is to slip a donut in where the gasket is supposed to go and tighten it up, you have to be careful you don't crush the donut.

Thanks for the tips. It sounds like you know exactly what I'm dealing with. I'll try these solutions. While I like most of the things in the Skyliner design, the exhaust flange and the exhaust pipe locations leave something to be desired. Running through those holes in the frame and over the emergency brake cable is a pain. I just wish we could order exhaust pipe sets made to fit alternative exhaust manifolds with a donut-style gasket and with a heat riser delete option.

when I make up pipes with Flat gaskets I make a Tube just a marginal amount larger than the head pipe ID and knock it in place . this sealer tube is 1.25" or so Tall !
use never seize on all sides of these tubes

I used to constantly develop leaks at the head and for the last 2 years I switched to a gasket made by RemFlex. I have not had a problem as of yet. The gasket is very thick.

I also kept getting leaks where the exhaust pipe connects to the exhaust manifold. I installed the 2 inch Remflex 2 bolt round gasket there and have not had a problem as of yet. Its only been out a few times since then so Im hoping it holds like the others held but so far so good.

I would definitely say its worth the try. Just be gentle when installing them.