In this paper, we analyse experiences of democratic practices in two research interventions within school contexts in Rio de Janeiro, Brazil. Both projects took place in public (Government-owned and managed) schools and were inspired by participatory and critical approaches, particularly Paulo Freire’s popular education and bell hooks’ feminist pedagogies. We analyse two case studies in which group interventions raise issues about democracy within schools and broader society, stressing the differences between the two contexts. The first case study discusses an educational programme for teachers and school staff on gender and sexual diversity, funded by a pro-diversity centre-left Federal government from 2007 to 2014. We analyse the group as a space to build multiple perspectives and democratic practices on gender and sexuality. Second, we analyse material from a project that conducted workshops with pupils (7 to 11 years old) to discuss interpersonal relations and the bonds they had with their schools during lockdowns (2021). Researchers developed participatory methods for remote learning and conducted online fieldwork with students—who had their parents’ and carers’ silent presence at home—analysing the construction of bonds with school, classmates and their autonomy. This project was conducted during a much more hostile moment than the previous one, during the COVID-19 pandemic lockdowns and in an ultraconservative political context in Brazil. While even during a social-democratic administration, we found limits in discussing gender and sexuality in schools (case study 1), the later authoritarian government and context severely worsened the situation (case study 2). Nevertheless, we were able to use critical approaches to promote and discuss democratic practices, especially considering gender, sexuality, race, and class inequalities. Through our practices as school psychologists and researchers, we make collective stands against authoritarianism.