A debris shield for a rotary tool or machine for collecting debris generated while cutting or drilling holes in a work surface has a debris collection housing having a top structure, side walls depending from said top cover structure to form a debris collection chamber, an open bottom with a surface contact rim, and a compression axis extending through the housing's top structure and bottom opening. In one aspect of the invention, the debris collection housing is a bellows housing with a vacuum port, and has a shank-holding and vent assembly in top structure of the bellows housing for receiving and rotatably holding the shank of a rotary surface working implement such as a drill bit, spade bit or hole saw.