First, I'm sorry for the long post, but I want to give as much information as possible. I recently acquired an '06 FLSTN with an oil leak. Makes about a 2"-3" diameter puddle after I park it. Once the oil cools, it will do 2 or 3 drops overnight. I've searched and read up on oil leaks on this forum and several others and have gone through my new service manual. I thought it was transmission oil. Oil was low when I got the bike (nothing on the dip stick), so not knowing what kind of oil was in it, I drained and replaced the oil with some 80W-90. I noticed it started leaking more (as described above) after I replaced the oil. The leaking oil is very clean and the same color as the transmission oil I replaced. But now I wonder if it's coming from the tranmission. Yes, the dipstick read full when I changed it, now, about 2 weeks and 150 miles later, it's showing low on the dipstick. But it appears to be leaking from the primary side of the pulley. See photo. Oil forms and drips from the outside of the pulley on the the backside of the inner primary, and then collects at a low spot near the drain plug, and then drips on the floor. After a ride, there is oil on the bottom of the frame tube. If I clean everything off, oil just drips from the pulley on to the primary. Nothing on the frame tube. So my question is: Is my transmission leaking oil and if so, what path is it taking to get to the outside of the pulley. After reading my manual, it makes more sense that it's primary oil leaking through the mainshaft bearing seal. I have yet to take my inspection cover off to check the oil level and see what color the oil is, I'll tackle this tomorrow. And other than leaving a mess, is this causing harm to my bike? I thought I'd try to fix it this winter, and although I'm mechanically inclined, it looks difficult plus you need some special tools. I've read that this is a 4-5 hour job and up here, at $95/hr, I'm probably looking at a $700 repair. Seems cheaper just to top it off when it gets low on oil. Or am I just asking for trouble? Thanks in advance for your help and suggestions. I enjoy reading all the Softail threads.

 

What you're showing here looks like a shaft seal is leaking. It appears that oil is coming from behind the pully. Looks like a tear down and inspection is necessary for a closer look.