This chapter offers a series of reflections on what I term ‘negotiating the impossible’, a phrase that seeks to capture the on the ground realities of the dramatic power imbalances and unequal battles between trade union representatives and employers, (dis)empowered by the combined force of Big Tech and Big Audit. The chapter draws on insights gained from across several research projects in which we have investigated the effects of digitalization on white-collar workers, new modes of algorithmic governance and management, compliance-oriented regulations, securitization of the workplace, and the role and possibilities of trade unions in negotiating the digital transformation. Using ‘exemplary examples’ from the Norwegian universities and higher education and finance sector, it analyses what I see as the key factors that in our current socio-political, regulatory, and organizational contexts ‘disarm’ trade unions and make their traditional arsenal ineffective vis-à-vis the hybrid forms of management, the infrastructural power of algorithmic architectures, platformization of governance and public procurement policies.