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I think you need more time to adjust to properly shifting gears. You don't need the strength (or attitude) of a gorilla to shift a Sportster. Just a nice simple click upward and you should be fine. Find a parking lot somewhere and practice.
John
I agree, if it was happening all the time then I would be concerned but once in awhile I would think it is more of the person doing the shifting rather than the transmission or lubricants.