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1991 Softail EVO Head Gasket Replacement -- Noob

You shouldn't have any air in the rocker box. Yours doesn't have the breathers/umbrella valves. They came about in 1993. You can run it with the top rocker box cover off if need be for testing for your air puff. Are you felling the air near the exhaust where you repaired the stud? If so then your header pipe isn't seated right or exhaust gasket leaking. If you feel air about 1.5"-2" below the rocker box then it is your head gasket.
tourbox

Thanks. I should've just gone further down yesterday. Learning... slowly.

Should I go all the base gasket too?
 
Checked the middle section of rocker box for warping on granite. 0.005”. Is that too warped?
Are you talking about item # 25 in this photo?

If so is it leaking from top or bottom of D ring? I wouldn't think .005" would make any difference. That could be from uneven chroming. I would find out where the air is coming from before removing Head though.
If you remove the Head you will have to replace the Base gasket also. Once Head is removed the torque/squish of the base gasket is disturbed.
tourbox
 
I was exactly talking about item #25.

Turns out the problem was this multipart-layered gasket the shop ordered for me. I didn't take off the o-rings off the dowels, so it messed everything up. I had to tear it all down and put it back together.

But got it together, did a minor push rod adjustment, and now it runs better than when I bought it six months ago. AND I now know how to replace all my engine gaskets.

Thanks for all your help everyone! It really made a huge difference.
 
I thought i had covered it however sometimes learning by experience reinforces the lesson
The bike is now sorted and valuable experience gained so the outcome is good

Brian
 
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