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After reading the responses I'm going to leave the derby cover alone for now, at least until I become a bit more familiar with the bike. Thanks everyone!
If you do remove the derby cover apply some never seize to the threads of the fastners before re-installing them.
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Frankly, I wouldn't remove the derby cover unless you absolutely have to. You can just add the tranny fluid through the primary chain inspection cover. I have had my derby cover off more times than I care to remember, but ONLY when necessary.
If you just insist on removing the derby cover, don't let the quad ring gasket come off. That is a royal PITA to get back in place sometimes.
Personnally, the first time I pull a derby cover off, I reach for the Milwaukee torx wrench. Had to on both bikes.
Drill the heads off, bolts will unthread by hand when cover is removed, replace with allen heads(stainless). Done.
Never have a problem again.
Go your trusty ACE HARDWARE and get the chome allen head bolts and swap them out. lf you will need to remove the cover if you plan on doing your services.
So are the Milwaukee Eight 5 hole derby covers different that the earlier 5 hole derby covers?
I just got an M8 powered 2017 Freewheeler and was planning on replacing the stock derby and points covers with aftermarket ones. Are the M8's a unique configuration vs earlier derby covers.
(God I miss the days when you could interchange nearly everything like you could on '36-'84 bikes.....)
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