Popcorn machines having automatic sifting systems, and associated methods of operation are disclosed herein. In one embodiment, a popcorn machine includes a cabinet for receiving popcorn and unpopped corn kernels. The popcorn machine also includes an automatic sifting system having a sifting component positioned at least partially within the cabinet to receive the popcorn and the unpopped corn kernels. The sifting component can include a plurality of perforations, and an agitator can be positioned to move the sifting component to agitate the popcorn and unpopped corn kernels. The agitation of the popcorn and the unpopped corn kernels moves the unpopped corn kernels toward and through the perforations.