Embodiments of the present invention provide systems, methods, and computer storage media directed to adaptable drawing guides. In implementations, a guide mode is identified. Generally, a guide mode indicates a manner in which to use a drawing guide to confine strokes corresponding with input paths. Upon detecting an input path, a stroke is drawn in accordance with the guide mode. For example, when an edge mode is employed, the drawn stroke is confined to align with at least one edge of the drawing guide, when an inside mode is employed, the drawn stroke is confined inside of the set of edges of the drawing guide, and when the outside mode is employed, the drawn stroke is confined outside of the set of edges of the drawing guide.