An information processing apparatus includes a controller including one or more processors and one or more memories. The controller receives attribute information of a printing apparatus from the printing apparatus, determines, based on the received attribute information, whether or not to generate a portrait image which format is a predetermined format, and rotates a landscape image in a predetermined rotational direction to generate the portrait image in a case it is determined the portrait image is to be generated. The controller also transmits the generated portrait image to the printing apparatus, and transmits information indicating that the portrait image has been generated from the landscape image.