The medication dispensing assembly includes a housing having an interior. A medication bottle is disposed in the interior with its cap assembly facing vertically downwardly. The cap assembly includes outer, middle, and inner pieces. The outer and inner pieces are fixed with one another, and the middle piece is fixed with the bottle. A drive unit is disposed in the interior of the housing and is configured to rotate the bottle and the middle piece of the cap assembly about a vertical axis. The three pieces of the cap assembly have respective medication openings, and rotating the bottle causes individual pills to travel first from the bottle into the inner piece, then into the middle piece, then around the vertical axis, and then outside of the cap assembly through the medication opening of the outer piece.