I have a 68 shovel srtoker95'. I let a friend return a favor...
Freshened up the top end, got it back and road around the block to find oil and exhaust coming out of the bolt hole on the front jug closest to the shifter.
Any ideas ???

 

Some ideas...head isn't torqued properly, head or cylinder mating surface isn't flat, crack in head from combustion chamber through oil return passage to mating surface on head, crack in cylinder (same route but through the cylinder, highly unlikely)...most likely, the problem is the mating surfaces/head gasket have issues. Did he check the mating surfaces with a straight edge? You could try retorquing the heads, they should be done after running it the first time.
I dig generator shovels.

 

Welcome to the HD forum Slowin..

What type of head gasket was used? any sealer or copper coat?
I use my curved snap on box end wrench and a hammer for the final tighten {tap tap tap} don't tell any one



let is know how you get your leak stopped.

 

I've always used fire-ring head gaskets on my shovel strokers The metal ID gives more leakage control

 

Yeah, recheck the torque on the head bolts. Sounds to me your problem is most likely there. Start with checking the simple stuff first, then check the head.

 

I wouldn't even mess around with it. If the exhaust gasses have gotten through as you say, I would pull the head and for sure put another gasket in after checking all of the above. The area it is leaking in is notorious for gasket leaks so take it all apart, check the surfaces and then, if everything is OK put back together using the same style gasket used in the rear. Torque in stages and start withe the bolt that is closest to where it leaked. Retorque COLD after the first heat cycle. BTW I use S&S copper gaskets on mine.