A pocket hole jig tool system includes a base on which a workpiece is supported. A drill guide support is slidably mounted to the base. Drill guide bushings are movably mounted relative to the drill guide support for clampingly engaging the workpiece and for guiding a drill for engaging the workpiece. A stop collar assembly is adjustably mounted relative to the drill guide bushings to automatically ensure a proper pocket hole location and depth for the workpiece inserted in the tool system.