230 Leaking oil at head/block

I figured I would post a new thread as some may not be following my restoration thread. I started and ran/test drove the truck today. I have oil leaking from the head/block seam on both sides of the engine, both leaks seem to be about midway more toward the front. Curious if anyone has experienced this kind of oil leak ? I my try a head re torque, the head gasket as far as I know is the original and the engine has sat for a long time.

If I do end up replacing the head gasket I have two styles of gaskets, one is metal and the other is fiber with metal around the cylinder holes. Curious which might be the best one to use

Thanks
UPDATE
I tried re torquing but no movement on the bolts so I figure it would be best to go ahead and change out the head gasket. I also think I am going to use the fiber head gasket as it's a bit thicker and I think it will seal better.

Make sure to get the right gasket,a civilian one will leak. I bought my truck with a uninstalled rebuilt engine . It leaked at the right front corner. Thanks to Barrman I got leak patched.

I have the correct gasket kit, thank you for the advice.

Can you post a photo-rich post of the procedure? I am about to remove my cylinder head to send it to the machine shop and I would like to see photos of the process. I am very familiar with working on engines and I have read the FSM on the issue. That being said, I also know that this could be a somewhat quirky engine.

OK I will try, I started today with not so good luck. I decided to take out the two special 11/14 bolts first so I would not mix them up, I was using my Makita 1/2 impact and just barely pulled the trigger and the head of 14 just came off like butter. I used a ratchet after that to remove the rest, I also had one bolt that was loose, guess what ? the bolt was snapped off at the threads so it looks like one drill/tap and the other should come out with vice grips, luckily I have a parts engine I can get the bolts from. I plan on taking the head off tomorrow and will picture how I am doing it.

Ok. Thanks. Do you plan on having a machine shop rebuild the head (valve guides, stem seals, etc.)? If so, DO NOT LET THEM RESURFACE (a/k/a "deck") THE HEAD. IT WILL RUIN IT.

No, it does not smoke and it has good compression, just going to clean it up and install new gasket. I have a metal gasket and a fiber gasket that was in some military gasket sets but I decided to purchase one of the new Best gasket graphite head gaskets, it should be here in a few days.

Removing head with timing cover in place. I removed the exhaust manifold to save on weight, remove rear oil feed line, I left the intake on but removed the carburetor, alternator brace, dipstick brace and associated lines going to the intake and temp sensor wire.

I used a plumb bob for reference and put a screw eye in the ceiling rafter about an inch forward of center to put a slight forward tension on the ratchet strap so once tightened it would pull the cam gear forward. I rotated the engine so the fuel pump rod eccentric was not putting any pressure on the fuel pump arm, this way there was no tension on either and no need to remove the fuel pump. I tie strapped the chain to the gear so there was no chance of it moving, also used a paint marker to mark it. I removed the bolt, lock washer and flat washer from the cam gear, as I removed it you could feel it move off the end of the cam quite easily and the cam gear never moved except forward, after the eccentric was off I pulled out the fuel pump rod and spring to allow the cam gear to come forward as much as possible. As a test I pushed the cam gear back on and alignment was perfect, nothing moved it just slid right back on.The only thing I can take credit for is the methods of non fuel pump removal, all the other tricks I found here by reading every post I could find on head removal. Next removing the head.

I rigged a chain hoist directly above and centered on the head, attached a strap and put some tension on the head, remember I still have one bolt minus the head still in the head in the worst place right up front where the head would bind against the timing cover. After some gentle prying and more tension she popped free and lifted straight off the block, rotated the head toward the driver's side then placed a 2x6 across the engine bay, lowered the head then slid it off across the plank.

The head gasket was not the correct gasket, it was a FEL-PRO 8023 civilian gasket with no wings on the front, so someone has been here before, would explain the broken bolts. I think I am going to use all the head bolts out of my parts engine as these may have been over torqued. Now cleaning and waiting for the new gasket to arrive. Oh, and the two broken bolt pieces just threaded out by hand, got lucky on that.

"Oh, and the two broken bolt pieces just threaded out by hand, got lucky on that." Home run!

Prepped the block by lightly sanding the surface with 150 emery cloth, also cleaned the thread holes with a 1/2-13 bottom tap and clean off any old gasket material from the timing cover. The gasket was missing from the RH side of mine, another source for the oil leak.

I cut the top of the timing cover gasket to match what is exposed with the head removed, glued them on the timing cover with some black rtv and let it sit for a day. I sprayed the new gasket with copper spray as per the instructions from the gasket company and let it dry for 10 minutes or so. I applied rtv to the end of the head that will mate with the timing gasket and a small amount at the intersection of the block and timing cover. I lowered the head so it was just above the block, slid the head gasket in then installed the two alignment bolts, be careful and try not to disturb the rtv on the end of the head as its a very close tolerance. Lowered the head on to the block then started the 4 bolts that go in to the end of the head through the timing cover, just finger tight. Inserted the head bolts and just snugged them down then torqued in sequence to 90ftlb. now you can finish tighten the 4 timing cover bolts. The cam timing gear slid right back in place, never moved a bit, torque to 40ftlb. Will finish up the external connections tonight and test run.

Initial short test run(no coolant)no leaks that I can see yet. Drove it for about half hour, all looks good so far, time to move on back to the restoration thread.