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if there is a faulty seal on the crankshaft then the gear oil can get to the crankcase
being a separate case with separate oil, check that the breather for the transmission is not blocked and the pressure build up is not forcing the oil past the seal into the crankcase
Harley recommends you use their 20w50 or Syn 3 (synthetic) oil. If you use Syn 3, you can also use it in the trans and primary. If you use conventional oil, Harley's Formula Plus goes in the trans and primary. Truth be told, any good high quality motorcycle oil (Amsoil, etc) made for air cooled engines will work in the crankcase.
I've never seen an online link but Chilton's sells a manual that will tell you most anything you want to know.
To change the oil, you must first drain the oil tank. Looking underneath the bike on the bottom of the transmission, you'll see two drain plugs. One will be in the middle of the tank and one will be towards the left side of the bike and slightly forward. The one on the left side and forward is your oil drain. Remove it to drain your oil.
While the oil is draining, change out the filter. Simply screw the old one off and install the new one. You may have to take the crank sensor out of the crankcase to get the filter out. Remove the screw holding it in, pull it out. When you get the new filter back on, reinstall the sensor. Don't overtighten the bolt holding the sensor in.
Now refill the oil tank. I think your FLHRS takes four quarts of oil. Put in three and check the level with the bike on the stand. Fill to the "Full Cold" mark is reached.
If you drain the transmission oil, remove the small plug and refill with 20-24 ounces of Harley Davidson trans lube.
If you wish to drain and change the primary lube, remove the drain plug on the bottom of the primary case and the "derby cover" over the clutch. Once drained, replace the drain plug and stand the bike straight up. Add 40-44 ounces of H-D transmission/primary lube or fill until level just comes to the bottom of the clutch spring.
Your bike originally came with Syn3 lubricant in all three places.
Fill the transmission with 20-24 oz. (590-710 ml) of
transmission lubricant or until the lubricant level on the
dipstick of the filler plug is at the F(ULL) mark with the
motorcycle in a level, upright position and the filler plug
resting on the threads.
Use only Harley-Davidson FORMULA+ TRANSMISSION
AND PRIMARY CHAINCASE LUBRICANT, Part
No. 99851-05 (quart).
6. Install the transmission filler plug/dipstick in the clutch
release cover. Tighten the plug to 25-75 in-lbs (2.8-8.5