A printing apparatus, having a container to store a printing medium therein, an acquisition device to acquire image data, a printing device to print an image on the printing medium, a cutter assembly to cut the printing medium, and a controller, is provided. In a case where a size of the image contained in the image data acquired by the acquisition device is smaller than a size of the printing medium stored in the container, the controller generates rotated image data containing a rotated image, which is an image rotated from an original posture of the image in the image data acquired by the acquisition device, controls the printing device based on the generated rotated image data to print the rotated image on the printing medium, and controls the cutter assembly to cut the printing medium having the rotated image printed by the printing device thereon.