Yes, it can happen. In the experience I had, it started with the engine revving to high before an upshift.
Example: The car would begin upshifting, would end up in what seemed to be neutral, rev up quite a bit, because my foot was on the gas, and then get into gear. At first this only happened when the tranny was cold, in the mornings.
A few months down the road it would do it periodically during normal driving, funny though, it never did it when I was WOT.
One day, entering the freeway, it wouldn't shift into 4th. I had to manually screw with the shifter, and it finally went in, had no more problems that day.
Not to much longer after that, the tranny just went out completely and wouldn't shift at all.
It could be the tranny fluid, but if you flush, and change the fluid, and this still happens...time for a new tranny