In implementations of path-constrained drawing with visual properties based on a drawing tool, a digital artwork editing system includes a user interface in which a constraint path can be designated in a digital artwork. A stroke input can be sampled as it is drawn with a drawing tool and for each processing interval of the stroke input, a start point of the stroke input and a tangent line to the constraint path is determined. An end point of the stroke input is projected onto a parallel line that is through the start point and parallel to the tangent line, and a stroke is rendered along this line. Hence, the stroke is rendered based on the stroke input in a piecewise linear fashion, simultaneously constrained by the constraint path and rendered based on how the drawing tool is used.