Disclosed is a self-watering-insert for placement within growing containers, the insert comprising a one-piece self-supporting structure having an open bottom end, a closed top end, tapered sidewalls, an open or closed interfacing structure that facilitates a secure seal of the insert against an interior wall of the growing container, an open collar on the top to allow temporary insertion of a pipe or water-discharging mechanism into the watering insert, a plurality of holes and/or screen/fabric material permanently attached to the surface of the top end, allowing water and air to pass through the surface. A lower flange extends circumferentially around the bottom end of the water insert, thereby creating a shelf upon which growing medium rests the flange further featuring downward protruding fins spaced so as to provide gateways through which water passes from underneath the interior of the watering insert to its exterior.