I have a 98 dyna wide glide that i bought used about three years ago which had a drain plug leak. when i went to harley to get a new drain plug they gave me drain plug kit with a white nylon washer and an o ring the instructions say to use either the white nylon washer or the o ring whichever came with bike. i have used the o ring when doing oil changes and it leaks the bike came with the nylon washer which eventually leaked too. i want to change oil before winter and just not sure what to use on this bike and harley gives me different answers. the bike came with the nylon washer but harley clerk told me to use the o ring and that did not work the kit number 60348-65b

 

I would try a Copper Washer of the same size as the Nylon .. Worked for me on my 2001 Sportster when wouldn't seal .. No guarantees but doesn't cost much to try it ..

 

Teflon tape on the threads will also help.

 

+1 on that as well ..

 

Just be real careful that bits of tape dont get into the oil system. It tends to leave taps in the threads when the plug is removed , then when reinstalling the plug it pushes thoes bits of tape into the engine case.

 

Yeah, I'd avoid the Teflon tape for that reason. Tiny threads of the tape will get into the oil system.

Not sure what the case looks like where the plug threads in, but if you can chamfer the hole enough so the o-ring fits in about half way (sits proud of the case by about half its diameter), then the plug (or plug with washer) will compress the o-ring into the space and seal the leak. The o-ring has to contact the shank of the plug as well, or it won't get squeezed into the chamfer. If the o-ring contacts the threads of the plug you will need to replace it each time you take the plug out, but it will not leak. (If it does, something else is going on...)

Or, get a "lock-o-seal" of the correct size: o-ring and washer combined.

 

Go to AutoZone and get a copper/o-ring setup like post 6. Having the copper ensures plug locks up. The O-ring seals. Good chance your threads have been repaired with Helicoil or insert. They leak around threads and original does not seal out far enough. If you are good with a fine file, a full face can be made to seal properly. Make sure you are good.

If the face is messed up, the copper/o-ring unit will need to be replaced ever time.

Later Harley's have a plain o-ring that seal in a bevel and the plug go metal to metal. Inserts or Helicoils destroys this function.