Abstract: The self-watering assembly is used in combination with a conventional planter having flow hole apertures formed within a base thereof. The assembly includes a set of water-permeable flow hole inserts each including a portion of capillary material such as spandex. The flow hole inserts are inserted into a flow hole of the planter for direct contact with soil positioned therein. The flow hole inserts are sized and shaped to securely fit within the flow hole preventing soil from falling out of the flow hole and preventing roots from growing through the flow hole. Additional capillary material, also formed of spandex, couples an interior of a water reservoir to the capillary material of the water-permeable inserts. By using spandex as the capillary material, sufficient capillary flow may be achieved to properly water even medium to large sized plants.