A delivery system includes a drone including a prime mover, one or more rotors operatively connected to the prime mover, and a payload attachment system including a latch mechanism having a first selectively deployable clamp member and a second selectively deployable clamp member. The delivery system also includes a plurality of nested reusable totes. Each of the plurality of nested reusable totes includes a body having a base, sides, and a lid, at least two of the sides include a gripping feature. The selectively deployable clamp members are operable to engage with the gripping feature on one or more of the plurality of nested reusable totes.