I've had to do that a couple times. You can watch it and see it's dragging slower, most of the time it catches up. A couple times it was too much and it stops before it gets to the tailgate and then I have to calibrate it again.
Passenger side tonneau cover drags a little slower than driver side, causing it to not close all the way and having to reset it ever so often.
Thinking some lube might fix it, anybody had that issue?