You never get all the oil out of the sump unless you use one of these
Harley Davidson Oil Change| Harley Davidson Oil Change Kit| Oil Change Harley

 

All the old oils put together should be 5-5 1/2 quarts. Did you ever check any of them before changing?

 

Like a dumb ***, no I didn't check anything. Lesson learned.

 

Well next time you will know ........I think it depends on the position of your bike when you drained the oil. If you had it on the jiffy stand or vertical on a bike jack. I drain mine while it's on a jack stand then I lower it and tilt it left/right to see if anything else drips out.
I also drain mine while it's still a little warm so the oil flows out easier......but really in the summer it's hot everywhere so that doesn't matter too much.
BTW welcome to the forum!

 

You'd be surprised how much oil doesn't drain out.

 

New o rings , I use pipe dope and new o-rings on my drain bolts. Always have. Don't over torque , use T27 on derby over not T25 .wrap you filter in a ziplock bag after you break it loose...some put aluminum foil under the filter to act as a funnel, I use non chlorinated brake cleaner after I put the new filter on....it cleans everything up nice.

 

And whatever you do, don't top it off to the full line on dip stick I found out the hard way. Two dipsticks later and oil blowing out the side like a geyser!

 

I just use the ounces and fill it that way... 38 oz Primary, 32 oz tranny , 128 oz motor, easy peasy. pour about 2 ounces in the filter before installing...

 

Good point............I don't use the pipe dope I use the Teflon pipe tape. I like the bag idea, I use a plastic bottle cut at an angle. Bag sounds easier.

 

No big deal...just put in the required oz in the tranny, primary. I put 2.5 quarts in the motor..start it and let it run till warm...finishing fill with dipstick quide. Your fine...