The 2007 demonstrations in Burma posed the greatest threat to military rule in almost 20 years. The involvement of thousands of monks across the country was of particular concern to the authorities as well as their threat of performing a religious boycott against them. The generals considered the threat of a religious boycott very seriously because, as in 1990, this threatened to demoralise the tatmadaw (armed forces) and questioned the loyalty of its soldiers and security forces, now almost entirely composed of Burman Buddhists. This paper traces the importance of Buddhism to the political legitimacy of rulers in Burma and examines how the authorities’ relationship with the sangha (religious order) has undergone significant changes under military rule. It compares the 2007 demonstrations with earlier protests and examines how the regime’s legitimacy has suffered as a result of yet another crackdown, significantly this time against demonstrations led by the largest institution outside of the tatmadaw. The involvement of monks in mass demonstrations against the military regime has undergone considerable change since 1988. The demonstrations of 1988 were in large part led by student groups and democracy advocates, with elements of the sangha taking part along with most representatives of civil society in Rangoon. Since 1988, however, the regime’s suppression of student activists as well as the closure of schools has meant that the sangha have adopted a higher profile in airing societal grievances and, as in 2007, in leading public demonstrations. And since the regime has all the guns, the monitoring personnel, and keeps the prisons well-occupied with political dissidents, the burden of opposition will from time to time fall upon the more passionate inside the monasteries. This will likely continue to occur until the regime’s leaders dare to step back once again and allow some form of civilian political opposition to arise. That the generals were able to suppress the demonstrations in 2007 says more about their own survival skills, in particular their tactical management of the situation and of their own security forces, than it does about their ability to foresee the events occurring. Now living luxuriously in Naypyidaw, secluded from the main populated centres, the top generals are so divorced from the suffering caused by their own ineptitude that the future possibility of urban unrest remains real. Added to this the fact that the generals have lost an enormous amount of legitimacy by committing violence against the very institution they are meant to support and whose traditions they promote, the sangha, and that it took only one visit by some of the monks to Aung San Suu Kyi’s home to inflame the demonstrations, means that they have a monumental task in garnering future domestic support for the regime. After 2007, the simple fact remains that the only claim the generals have to running the country is that they hold all the guns. The move to Naypyidaw has meant that they are now more remote and alienated from the general community and, most importantly, less in contact with the local communities than is the sangha. Because of this, the shift to Naypyidaw may lead to a more fragile state than they had bargained for at the time. It is uncertain, however, whether the younger monks involved in the 2007 demonstrations will continue their fight after the crackdown. Many will have shed their robes voluntarily. But for those that remain, they will have surely been emboldened by the experience, perhaps their first real taste of what deeds this regime is capable of. Because the sangha remains the only sizeable, potentially rapidly organisable, and morally dangerous opposition in Burma, with the passing of the older loyal sayadaws (senior abbots) the tatmadaw must continue buying the loyalty of the younger monks. Yet because of the size and significance of the 2007 demonstrations, which far outweighed the sangha’s involvement in both the 1988 demonstrations and the more localised protests of 1990, it is difficult to see their loyalty forthcoming.