In this talk, I argue that unconventional ways of political contention successfully shape the regime, its elites, and its forms of oppression even under the most authoritarian contexts and repressions. Using the context and temporal development of the Kazakh Spring protests (2019-ongoing), I focus on how the interplay between the repressive regime and democratisation struggles define and shape each other. Combining original interview data, digital ethnography and contentious politics studies, I argue that the new generation of activists, the likes of Instagram political influencers and renowned public intellectuals, can de-legitimise and counter one of the most resilient authoritarianisms and inspire the mass protests that none of the formalised opposition ever imagined possible in Kazakhstan. The talk will conceptualise how the post-Nazarbayev Kazakhstan struggles for its path to democratization.