A text-on-path graphic is automatically created from entered text and a drawn shape having a complex path. Shape boundary curves are identified from the shape. A set of overlapping boundary curves is determined from the shape boundary curves. The set of overlapping boundary curves is combined into a combined curve. The combined curve and the shape boundary curves outside the set are assigned to segments of the complex path. A cost for each ordered path through the segments is determined, where the cost of each ordered path is based on a distance to a next segment and a length of the next segment. The text-on-path graphic is then created from the text and the ordered path having the lowest cost.