TOPIC:

I did some maintenance on the bike on Monday. Cleaned the carbs and checked the valve clearance. The only clearance out of spec was on the #3 intake. I corrected that issue and put the bike back together. Started the bike up and it ran good. Put the bike away and took it back out today. Started it up and noticed that it wasn't running right. I checked the pipes and the #4 pipe was not hot. The other 3 were. I then noticed oil squirting out from where the #4 pipe connects to the head. I took the pipe off and didn't see anything out of the ordinary on the head. Put the pipe back on and it was still squirting oil from the #4 pipe at the head. Anyone have any idea's as to what would cause this problem ?

It is possible that the part of the cam cover gasket that goes around the Clean Air port for #4 got torn or folded over and oil is being sucked into the exhaust port. Spraying out suggests that the exhaust gasket is also toast.

Is the oil leak above or below the exhaust pipe?

After I put the bike back together, I had it idling and it looked like it was squirting out right next the where the pipe connects to the head. Don't think it is from the cam cover gasket. Could it be the head gasket or the valve stem seal on the #4 exhaust port ?

The only leaks I've had were from the cam cover plugs and head gasket at the #4 corner. Neither were considered as possibly coming out of the exhaust port, as it was evident where the leaks were coming from.
When the head gasket leaked, it was due to a lost seal at the o-ring where the oil passes through the head along the stud on that front corner. Once the original studs were replaced with a APE HD studs and nuts, that problem was eliminated.

Did you check the spark plugs? sometimes the oil can travel unseen.

I started the bike again to check on this. Still seeing oil squirting from the the #4 header pipe. I took the header off and there are no gaskets on the head. Not sure if there should be or not with a V/H header. Still unable to figure out why oil is squirting from the exhaust port. I tried taking a video of it, but it didn't come out right.

Would replace all four exhaust gaskets with brand new gaskets.
Be sure to first remove all old gaskets, remembering that there could be more than one old gasket inside a port, because someone might have installed two or more old gaskets instead of using a new gasket. The old gaskets are hard, black and encrusted so as to be difficult to see. So keep scraping and pecking away until positive that the port is clear of old gasket material.

When the exhaust system is properly fitted, no oil can escape past the gasket, and any liquid oil in the exhaust will likely exit from the muffler or wherever the exhaust normally exits.

Good Fortune!

Thanks for the info, I checked the head and there is not gasket on any of the exhaust ports. I have scraped all 4 ports and ordered new gaskets. Hopefully that will fix my issue.

BIGKEVIN wrote: Thanks for the info, I checked the head and there is not gasket on any of the exhaust ports. I have scraped all 4 ports and ordered new gaskets. Hopefully that will fix my issue.

If you have oil literally squirting out of the #4 exhaust port, then there must be a larger problem than not having an exhaust gasket in there. Is there evidence of oil on the valve stem (or around the valve guide), visible while viewing through the open port with the exhaust removed? That would suggest a bad valve-seal, or loose fitting valve guide...neither issue which any kind of exhaust gasket will fix.
Just can't imagine any other source where that oil could be coming from.

If I looked into the #4 exhaust port with the header removed from the port, the valve stem was wet, like oil had gotten on it.

If it is coming out of the port it's either a valve stem seal or piston ring problem.
When riding the bike if it smokes all the time it's rings.
If it only smokes on the overrun it's stem seals.
Another check for the stem seal is to remove the exhaust.
Clean the offending port of all oil and leave the bike on the main stand overnight with the exhaust valve closed, if the stem seal has failed fresh oil will be seen to have run down the stem and into the exhaust port.