to all who have posted to this thread about this issue THANKS. I stepped up from an 01 Road King (awesome bike) to an 08 Electra classic with 5k on it. I have not heard of or paid particularly close attention to this and am ready to leave "the place were i go to get paid" to check it out. AGAIN THANKS GENTS FOR THE INFO
I have heard this connected with touring bikes but it may be the others as well. It's mainly on the transmissions with the end cover that has the dipstick mounted through the cover and not in the case like on the 96 engines.
This is the problematic area. The early 96 engines had a different problem of the dipstick breaking off the cap itself.
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Pretty much the same setup with the dipstick. It's not an epidemic but it only takes one dipstick to trash the trans.
Pick up another dipstick and cut off the dipstick end of the unit and use it as a plug in place of the dipstick you save for checking the oil level.