This article centers on tsarist Russian officials’ understandings of and approaches to the Iranian Constitutional Revolution (1905–11). Although these officials relied on fragmental information and reflected internal discoordination in their dealings with Iran over the course of the revolution, a diachronic shift marked the policies they formulated in response. Although many of them attempted to navigate the Constitutional Revolution’s complexity in its early phases, they tended toward the use of force as unrest continued, culminating in the Russian invasion of northern Iran in December 1911. Uncritically confident in their exercise of power, Russian officials proceeded without considering alternative courses of action or the potential costs of military engagement in the revolution’s final stages. This heavy-handedness reflected continuity with the tsarist government’s crackdowns on socialists in the Caucasus after the Russian Revolution of 1905, and presaged its repressive, self-defeating responses to uprisings across the Russian Empire from 1912 to 1917.