This paper offers a broad historical and comparative analysis of territorial organisation and autonomy in Russia from the early modern age to the present. To what degree, when, and why did the Russian and Soviet authorities accommodate and even promote regional and national autonomies on their expanding territory? The paper reviews efforts at decentralisation (and in some cases federalisation) as a set of imagined, proposed, and (partially) implemented measures. In so doing, it identifies historical ‘moments’ at which autonomous solutions became particularly important. It also highlights commonalities and differences, continuities and ruptures in longterm perspective while tracing the specificities of the Russian case. While different forms of territorial autonomy coexisted throughout Russian history, most were shortlived or heavily constrained.