I was taking off my valve cover to change out the gasket to stop it from leaking. When I took off the 2nd bolt from the front on the drivers side, coolant started coming out of the bolt hole! It does not leak when the valve cover is on. There are no other leaks and the engine does not run hot. Should I be concerned?

I have heard of someone using too long of a bolt on the side cover and driving it into the water jacket. Perhaps that happened to your head at some point. Just install a stud in the bolt hole using sealer or epoxy and tighten the cover with a nut.

It is very possible like French said. This is also known to happen when The First stud is removed from a stock head Changing over to header and installing New Bolts.If to is to long it can cut/push the back of the hole out and start to leak water as well.

I to have had a Few factory Untouched heads Leak
Like that. Just be sure to use sealer on the one Or Like french said Stud it and use sealer.

Thanks gents. I will I will keep an eye on it and I will put a stud in place of the bolt.

Some of the holes in the 250 type heads have very little meat on the bottom and easily will break through unless a stock length screw is used. A regular 1/4 - 20 screw or bolt can be used if you just apply some silicone sealer to it before installing. It will seal fine. A stud may be a better idea because with a screw you need to drain down the engine of coolant if you want to remove the valve cover.

Either method is ok and not a major problem as long as you let the sealant cure a bit before refilling with anti freeze.