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Dyna Glide ModelsSuper Glide, Super Glide Sport, Super Glide Custom, Dyna Glide Convertible, Super Glide T-Sport, Dyna Glide Police, Dyna Switchback, Low Rider, Street Bob, Fat Bob and Wide Glide.
You're checking the fluid level incorrectly. The bike should be standing straight up, not on the side stand.
Also as mentioned before, you remove the dipstick and then just rest it on the opening. Do not thread it in to check level.
Lastly that appears to be an aftermarket dipstick? Not sure how accurate it is. But a way to test would be to drain fluid, catch in a clean container if reusing, and measure the required amount for that transmission (20-24 oz approx) and see where it is on the dipstick for future reference.
Edit: I now see that dipstick had HD on it but you can still check correct amount in transmission by above method if you wanted to.
With Dynas you check oil and tranny with it on the kick stand.
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