A printing apparatus configured to print a label image on a medium, the medium on which the label image is printed including: a first end which is an upstream end of a tail region in a conveyance direction that is one of first printing regions in which one first character is lastly printed; and a second end which is an upstream end of a tail character in the conveyance direction that is the most upstream one of second characters printed in a second printing region, and wherein a controller is configured to cause a cutter to cut the medium at a first cutting target position located upstream of the first end when the first end is located more upstream than the second end and at a second cutting target position located upstream of the second end when the second end is located more upstream than the first end.