The progressive digitalization of industries and services has direct effects on the organization of labor. Telework is foremost a consequence of the general increased use of information technology in our professional and private lives. The organizational changes of labor due to digitalization however challenge the functionality and effectiveness of labor law. The employer’s comprehensible concerns, that teleworkers might pursue private interests at home, serve in practice as a justification for implementation of closed meshed monitoring measures. Hence, we face a significant paradox: even though teleworkers enjoy a putative higher degree of autonomy because they are not present at premise and therefore not subject to the employers’ physical authority, they are exposed to a higher degree of dependency rooted in digital control measures. Data protection acquires increasing importance for workers. Labor protection in many cases cannot be separated from data protection. This chapter argues that this evolution is not sufficiently mirrored by the law, and then analyses in its first part the existing shortcomings and loopholes exemplified by the problem of digital surveillance of telework. In its second part the chapter seeks to identify possible legal mechanisms to create or even foster interaction between labor and data protection law.