Does the transmission always try to learn driving habits? I bought my 2015 used which was a work truck, will tranny relearn?

 

No, it doesn't learn driving habits. It learns how long your particular transmission takes to complete a shift from when the computer commands the shift until it measures the shift has completed. It then adjusts pressures to bring the shift time back to the programmed ideal time.

Learning continues for the life of the transmission. It makes no difference if you bought it used, driving habits do not affect learning.