Motorcycle Repair: Harley Drain Plugs, oil drain plugs, teflon sealant

Question
I finally have the time to do my own maintenance on my '03 softail. I've located all the drain plugs for the primary, transmission and oil but I'm not sure about the tool I'm using. The plugs appear to be T-40 torx but the bit seems a little loose and I don't want to strip the heads. Am I using the right size? Thanks

Answer
Your primary chaincase drainplug is a T-40 under the rear area of the primary.  It's a pipe thread (tapered) and sometimes has teflon sealant from the factory.  Clean the threads before replacing. Just don't overtighten when replacing.  Your motor oil drainplug is on the right rear frame crossmember just in front of the rear wheel.  It is a 5/8" hex with a 1/4" allen hole in the center.  Your tranny has the same plug type and is up between your softail shocks.  When replacing the tranny plug use an allen because a socket will cock it and crossthread it cause it's too close to the left shock. DO NOT try to remove any plugs on the engine crankcase!!!  You can crack the case.  Make sure you run the bike for 3 or 4 minutes before draining the motor oil.  This gets any oil out of the cam cover and crankcase and back into the tank.  The bike must be standing straight up to get all the oil out of the tank and the tranny when draining.  Refill with 3qts. motor oil, 20-22 oz. tranny oil, and 26 oz. primary oil.  Fill the primary through the inspection cover hole (four T-27 bolts hold it on).  And replace the inspection cover gasket(60567-90D)  Check the o-rings on the tranny and motor oil drain plugs. They flatten out and get frayed after awhile.  If need be, replace them with #11105 o-rings.  Good Luck!  PS  I recommend just using the Harley filter also.  #63798-99A