Unionized organizations are implementing more than ever technological changes to cope with an increasingly changing and highly digital environment. Despite the extensive literature on union responses to changes, there is not much evidence on how unions and employers draft provisions pertaining to technological changes in collective agreements. Therefore, this paper aims to conduct an in‐depth analysis of these provisions in over 500 collective agreements signed between 2000 and 2020. Specifically, this study focuses on office workers in two of the most important Canadian industries, namely, the healthcare and manufacturing sectors. The findings indicate that within the examined provisions, the regulation of technological change varies along a continuum that extends from no obligations to stringent obligations on the part of the employer. Moreover, the results show that these provisions have remained stable over the past two decades.