This article examines the issue of democratic breakthroughs in highly geopoliticized, fractured regions in the post-Soviet space. While recognizing the political challenges of democratic transitions in such regions, it investigates specific conditions conducive to effective democratic openings in such regions. Using a case study method, it focuses on Armenia’s Velvet Revolution in 2018, which successfully challenged the previously-entrenched authoritarian regime in the country. This was particularly significant as it occurred in Russia’s security orbit. Armenia has been firmly wedged in Russia-centric regional organizations, in parallel to the deep bilateral ties between the two countries developed since the Soviet collapse. This article argues, first, that the efficacy of nonviolent civil disobedience campaign played a key role in ushering a peaceful democratic breakthrough. This strategy is also credited for explaining Russian restraint as the events unfolded throughout the year. Second, it also highlights the specific form of Armenia’s authoritarianism and the institutionalization of the state that it had produced. It posits an autocrat’s dilemma: greater state institutionalization to defend the “soft” authoritarian system at some point becomes a liability. This dual-track approach to the study of Armenia’s Velvet Revolution, the civil society and the state, is also used to explain Russian restraint as a factor in this case. The article concludes with a brief application of this dual-track transition model to the unyielding mass protests in Belarus, also occurring in Russia’s security orbit.