Eswatini is an absolute monarchy. Political parties have been banned since 1973 and the common citizen is virtually excluded from political power. However, from the 1980s, civil society organisations were allowed to form, giving rise to trade unions that became the focal point of pro-democratic demands in the following years. Focusing on the 2018–2019 pro-democracy protests in Eswatini, this chapter argues, that both organisational resources and political opportunity structures (POS) were important to explain the emergence and the limited impact of protest in the country. First, trade unions were able to build on their resources and legitimacy to organise and sustain protest. Second, discursive political opportunities (legacies of unions work throughout the 1990s and first decade 2010s) contributed to create resonance with pro-democratic frames. Third, the presence of allies – namely political parties and international actors – contributed to the creation of further pressure for change. The chapter will rely on documentary research, in-depth interviews, and a content analysis of protests covered in the mainstream newspapers. The findings contribute to debates on protest in authoritarian settings.