Dipstick reading

Dumb question, and I'm a newbie to cars but I'm getting ready for a summer road trip and going over all the essentials.
No issues at all with my transmission shifting, but when checking the dipstick per the FSM in HOT and NEUTRAL i get two reading on my dipstick. One side marks fluid very high up (overfilled) while the other side marks fluid very low (Add 1 pint).

I don't want to overfill the trans. Which side of the dipstick should i trust and is there a specific way to insert the dipstick? Thanks