Digital image dynamic shadow generation is described as implemented by a dynamic shadow system using one or more computing devices. The dynamic shadow system is configured to generate shadow objects based on one or more source objects included in a digital image (e.g., a two-dimensional digital image), automatically and without user intervention. The shadow object is based on a shape of the source object that is to “cast” the shadow and thus promotes realism. The shadow object is also generated by the dynamic shadow system to address an environment, in which, the shadow object is disposed within the digital image.