In the context of digitalization and Industry 4.0, the world of work is changing comprehensively. Smaller lot sizes and increasing variability of products in the modern industrial production present new challenges for operators working in manual assembly. Industrial assistance systems help the worker during these production tasks to enhance their capabilities. The development of these systems is not only characterized by questions of the potential feasibility of new technical systems but also by the possibilities of a closer cooperation between humans and machines with the aim to synergize the outstanding abilities of humans with the special features of machines to bring together the best from both worlds. This chapter presents solutions for human–machine interaction and automation and delivers insight into different possibilities to enhance the various types of operator’s skills in industrial assembly. With this knowledge, each worker can be individually equipped with suitable supporting systems in order to be best prepared for future challenges in the daily production.