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After mentioning both the complexities of defining penal supervision, and the evidence about its significant growth and intensification, we will focus on three paradoxes. Is supervision a form of liberation or a deprivation of liberty? Is supervision punishment or is it not? Is the lack of public support for supervision an obstacle to its development, or has it been critical in its development and diversification? In important senses, the meanings of ‘community’ in community sanctions and measures lies at the heart of all three paradoxes. For example, in relation to the first and second paradoxes, it is often assumed that to be in the community is to be at liberty, and remaining in and of the community is not consistent with (really) being punished, however punishing it may be. In relation to the third paradox, perhaps the question is whether supervision can be for the community and with the community. We will argue therefore that if community sanctions and measures are to fulfil their aspirations to reduce the damage that punishment does and to enhance social reintegration, then we will need to pay more careful attention to precisely when and how we involve the state, and when and how we involve the community, in their design and in their implementation.