When reinstalling the drain plug, every time I tighten the plug it cuts the o-ring about 2 rounds before its tight. It doesn't leak, but what am I doing wrong?

 

Not sure that you're doing anything wrong...?

Not that you can't use them more than once, but they are a wear item.

All the best,

Shane

 

O-rings are designed to fit in a channel. You don't by any chance have an old O-ring stuck within the channel so that you're double stacking rather than replacing ?

 

little bit of oil on it before you tighten will often help

 

Oiling is the better way to do it as SIDECAR BOB said

 

Are you sure you got the right o ring?
I buy the bag sealed from Harley just to make sure I got the right o ring.
I know guys say they buy them from the hardware store etc but I don't know what that size is called and I'm not going to try to "match it up".

The only time I've cut one was by over tightening the plug itself. There is a tq in the service manual. I follow it. And I get hd o rings. No leaks, no cuts.

 

You can find the right O rings for less on here:
https://www.hdforums.com/forum/gener...g-o-rings.html

 

You can find an oil pan on Ebay for under a $100 and about $170.00 new, from Harley, plus the $10 pan gasket.It's about a 3 hour job to swap it out. Once it cracked, its only going get worse with heat changes ,vibration and you trying to change the oil. The only right way to stop a crack in metal is to, drill a hole at the end of the crack, v out the crack, and weld it up.That ain't happening on the bike! Not to mention, good luck having a weld take, with porous aluminum soaked with oil. Fix it right and put it to rest. Does it suck? Yes! But if you are keeping it, do you want that issue in the back of your mind every time you go for a ride?

 

Also make sure the crankcase is clean.

 

I have always had trouble with the Harley 0 rings. I went to the auto store and bought some just one size smaller but the same thickness the price was around 30 cents each compared to the $1.10 each at the dealer. No leaks for over 20,000 miles, I put a new one on every oil change though.