The Central Himalayan region, until the medieval period, was under the possession of a confederacy of many independent and semi-independent principalities and kingdoms known as the Baisi and Chaubisi Rajya. Wars were frequent, and the restructuring of territory remained a work in progress, as the region was engulfed in conflict for more than seven decades until the territory was unified into a modern state of Nepal. Nepal’s path to modern statehood continued under oligarchic rule, particularly during the Rana regime (1846–1951), characterized by a rudimentary stage of governance and an ad hoc understanding of sovereignty. The chapter contrasts the conceptualization of sovereignty and territoriality under the Shahs with the Ranas. A key focus is placed on how connectivity was strategically used by the Shah rulers to facilitate territorial expansion, while the Rana regime adopted anti-connectivity policies to consolidate internal control and limit external influence. It also examines the role of geopolitical agents in reinforcing sovereignty, undertaking the process of territorialization and discouraging foreign intervention. Despite these divergent approaches, the chapter explores the reason behind a consistent strategic interest in the trans-Himalayan region. Overall, the chapter explores whether connectivity, transit and balancing policies—considered indispensable to modern Nepal—were given equal importance in its historical context and how connectivity remained central to Nepal’s geopolitical calculations during this period.