On the freeway, does it lock into overdrive?
I'm not sure about the paticulars of your truck but once the torque converter locks up, the heat generated by pumping transmission fluid drops dramatically as it's no longer being asked to transfer power between the engine and transmission.
In city driving, the fluid is doing most of the energy transfer and that generates heat especially if you do a lot of hard acceleration.
Secondarily, in city driving less air is passing over the trans cooler due to slower speeds.
This is why you get a counter intuitive temperature reading with lower temps when you are putting out more power on the freeway.