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What can be some of the things that would cause a hard engaging transmission ? Seems like when I put the bike in gear it seems to go in harder than normal.
If the clutch is adjusted correctly, try a better Primary oil. And i don't mean the Harley Brand oils. I use Drag Specilties Big twin Primary (Me and my friends love it). But I hear a lot of good things on the Redline oils also. This is of course the cheapest and easiest thing to try to change. I tried the Syn 3 20/50 in my Primary and the clutch did'nt seem to desengage as good as when I had a no name cheap Primary oil in it. Just my .02 cents worth.
That's one reason I run ATF in my primary. The clutch seems to disengage better with it. I would try what the above post says and try an adjustment and a different fluid.
Also might try gear oil in the tranny. Harley doesn't recomend the syn 3 in all three holes anymore. Also, when the bike is cold, work the clutch lever a few times before dropping it into gear.
Best thing to do is the clutch pack adjustment. Sometimes the locking nut can rattle loose causing the adjusting screw to come loose. Also adjust your cable to where you have 1/8" gap when pulling the ferrule away from the perch. Manual has a good write up.
I had a clunk when putting in first gear but switched to B&M Trick Shift at the recommendation of various forum members and the clunk is gone and shifting is smooth.