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I've never heard of a h. gasket giving way to an oil passage, but for the last 5-6 days I've noticed a rather large cd size puddle under my truck where the trans should mount to the engine. Today I finally fought off the lazies and took a peak between the v.cover and firewall. The passenger side of the block is covered with oil. I felt it and smelled it. It is oil. I don't have coolant in the oil. But I can see where the oil originates at the junction of head to block. There is no sign of oil above that gasket line.
Tomorrow I'll remove the v.cover and take a peak at the head bolts/studs back there. Right now I really don't know what is going on, other than I have a major oil leak, and, I'm afraid to say it, a minor miss. Coolant levels are dropping slightly. I know I need to do a compression test.
I don't think the 300 head has oil pressure to it. Are you sure it isn't leaking somewhere else, like the valve cover gasket (maybe near the front of the engine) and running down until it hits the gap between the head and block, then traveling down that gap until it finds a place near the back of the engine to spill out?
I'm with Jim. I cannot think of any pressurized oil passage in the head. All valvetrain oiling is done thru the pushrods. A blown/leaking head gasket in the area of an oil drain hole could cause oil to leak, but doesn't the 300 use the pushrod holes as drains? Those are on the wrong side of the block for this to be possible.
Truly stumped here......
I'm with Jim. I cannot think of any pressurized oil passage in the head. All valvetrain oiling is done thru the pushrods. A blown/leaking head gasket in the area of an oil drain hole could cause oil to leak, but doesn't the 300 use the pushrod holes as drains? Those are on the wrong side of the block for this to be possible.
Truly stumped here......
I do not know how the oil returns to the crankcase on the 300 (I have not needed to remove the valve cover on mine) but I worked on a buddies old 351M that was leaking oil big time from under the valve cover. What I found was the oil return hole at the fire wall end of one head was completely blocked. This was a sludge motor. Hopefully the OP will not find anything like this.
It was difficult to get in between the firewall and head with a light and a mirror, but I managed. As RW suspected, I found where the oil was running down. Once I got the v.cover off I found it was split.
The Clifford v.cover is a pain. They make it a slightly different shape so you have to get replacements from Clifford's Performance. And of course that costs more. Instead of dealing with them, and paying more for postage, I took one of the cork gaskets I had left over from a kit, and trimmed it to fit. I cleaned the cover real well, and glued the gasket to it with weather strip adhesive, and clamped it in place where it didn't want to fit. It always takes me about 30 slight twists on each bolt, with a 1/4" drive, to get the cover tight, without, hopefully, splitting the gasket. I had to enlarge a couple of the holes too. It allowed me to change the color from blue to black. Now it is all sealed up and I no longer have the CD size puddle beneath the truck. A trip to the car wash gun will remove all the oil from the engine.