Due to the innovative possibilities of digital technologies, the issue of increasing automation is once again on the agenda – and not only in the industry, but also in other branches and sectors of contemporary societies. Although public and scientific discussions about automation seem to raise relevant questions of the “old” debate, such as the replacement of human labor by introducing new technologies, the authors focus here on the new contextual quality of these questions. The debate should rethink the relationship between technology and work with regard to quantitative and qualitative changes in work. In this article, our example will be the introduction of automation in industry, which has been reflected in the widely recognized study by Frey and Osborne in 2013. They estimated the expected impacts of future computerization on US labor market outcomes as very high, specifically regarding the number of jobs at risk. Surprisingly, this study was the starting point of an intensive international debate on the impact of technologies on the future of work and the role of technological change in working environments. Thus, according to the authors, “old” questions remain important, but they should be reinterpreted for “new” societal demands and expectations of future models of work.