Rotating a piece of paper while drawing is an integral and almost subconscious part of drawing with pencil and paper. In a similar manner, the advent of lightweight pen-based computers allow digital artwork to be rotated while drawing by rotating the entire computer. Given this type of manipulation we explore the implications for the user interface to support artwork orientation. First we describe an exploratory study to further motivate our work and characterize how artwork is manipulated while drawing. After presenting some possible UI approaches to support artwork orientation, we define a new solution called a rotating user interface (RUIs). We then discuss design issues and requirements for RUIs based on our exploratory study.