People with disabilities are severely underrepresented in the open labor market. Yet, pursuing a job has a positive impact in many aspects of life. This paper presents a possible approach to improve inclusion by including a robotic manipulator into context-aware Assistive Systems. This expands the assistance possibilities tremendously by adding gesture-based feedback and aid. The system presented is based on the intelligent control system of behavior trees, which—together with a depth camera, specifically designed policies, and a collaborative industrial robotic manipulator—can assist workers with disabilities in the workplace. A developed assistance node generates personalized action sequences. These include different robotic pointing gestures, from simple waving, to precisely indicating the target position of the workpiece during assembly tasks. This paper describes the design challenges and technical implementation of the first Context-Aware Robotic Assistive System. Moreover, an in-field user study in a Sheltered Workshop was performed to verify the concept and developed algorithms. In the assembly task under consideration, almost three times as many parts could be assembled with the developed system than with the baseline condition. In addition, the reactions and statements of the participants showed that the robot was considered and accepted as a tutor.