This paper examines non-compliance with community penalties from a wide point of view (without attaching it to a specific jurisdiction). It argues that there is a systemic need to respond to non-compliance of a penal sanction. It also describes the impossibility of enforcement of penal sanctions that are supposed to be executed in liberty and the possibilities of the penal system to react to that kind on non-compliance. These possibilities are analyzed from the proposals made by the two main groups of theories of punishment (retributive theory and deterrence theory). Finally, legal consequences to non-compliance in the Chilean legal system are studied (law and jurisprudence), comparing them with the standards and proposals developed earlier.