Vladimir Putin has been the undisputed leader of Russia (either as president or prime minister) for almost 25 years. Barring an accident or assassination, Putin seems almost certain to surpass Joseph Stalin's record long reign over the Soviet Union of 29 years. The durability of Putin's regime comes despite a record of endemic corruption, poor governance, economic growth that gave way to recession, a poorly managed COVID response, and a disastrous invasion of a peaceful neighbor in 2022. Despite all of this, Putin endures. How does he do it? A new book by Hannah Chapman, Dialogue with the Dictator: Authoritarian Legitimation and Information Management in Putin's Russia is a welcome addition to a lengthening list of recent studies seeking to explain the resilience and potential vulnerabilities of authoritarianism and of Putin's regime in particular. In one way or another, all of these books focus on the question that also puzzles Russia's opposition politicians: Why is Putin's autocracy so resilient? Chapman offers one answer in exploring the ways in which his regime uses “participatory technologies” to not only enhance regime legitimacy from Russian society but also to control what information reaches Russian citizens. This article reviews her book in the context of other recent studies of how Putin's autocracy works and why it has lasted so long.