A chalk box assembly for providing an automated retracting chalk line comprising: a chalk box housing; a spring assembly within the housing; a spool for retaining a chalk line within the housing, where the spring assembly is attached to the spool and provides for the retraction of the chalk line; a chalk compartment within the housing, where chalk is stored within the chalk compartment; and a retraction button engaged with the spring assembly, where the button causes the release of the spring assembly for the retraction of the chalk line. The chalk box assembly according to the present invention may further include a chalk line guide and a chalk fill door. In one particular embodiment of the present invention, the chalk box assembly further includes a belt clip on one side thereof.