The thesis examines the process of digitalisation of the enforcement of criminal sentences, with particular attention to surveillance proceedings, identified as a privileged field for assessing the compatibility of the digital justice model with the structural and functional specificities of the enforcement phase of criminal proceedings. Starting from the awareness that the digitalisation of justice does not consist merely in the telematic transmission of procedural acts, but rather entails the creation of a genuine technological ecosystem capable of managing information flows, case files, and decision-making processes, the research investigates the normative, institutional, and technical conditions necessary for this process to be both efficient and respectful of the safeguards inherent in surveillance proceedings. The analysis begins with an examination of the supranational context, within which the impulses towards the digitalisation of justice have progressively emerged; it then proceeds with a reconstruction of the development of computerisation in the Italian criminal justice system, focusing on the legislative, organisational, and cultural stages that have led from the analogue management of proceedings to the construction of the current ecosystem of the telematic criminal process. Particular attention is paid to the governance of judicial IT systems and to the role played by the Covid-19 pandemic as a factor accelerating reform processes that had already been initiated but had long remained incomplete. The central part of the research examines the model of the “digital environment” of criminal proceedings introduced by the Cartabia reform, with specific reference to the new configuration of procedural acts, electronic filing, and the digital case file. The analysis highlights the strengths and weaknesses of a regulatory framework characterised by a high degree of flexibility and by extensive reliance on technical regulatory sources, focusing in particular on the systemic risks associated with regulatory fragmentation and the potential repercussions for the right to defence. The study shows that the assessment of the digitalisation process cannot be limited to the normative dimension alone, but must necessarily engage with the level of technological infrastructures responsible for its concrete implementation. An examination of ministerial software applications reveals operational shortcomings, structural rigidities, and organisational misalignments that risk affecting the effectiveness of judicial protection, assuming particular significance in the enforcement phase. In light of these elements, the thesis uses surveillance proceedings as a testing ground for the digital justice model in the enforcement phase of criminal law, demonstrating how the extension of the telematic criminal process to this area requires a rethinking of infrastructural and organisational architecture, so that digitalisation may translate into an actual improvement in the quality of judicial responses. The study thus identifies the fundamental prerequisites—at the institutional, technical, and organisational levels—that an operational model must possess in order to be compatible with the peculiarities of surveillance proceedings, highlighting how, in the absence of such conditions, the risk is that of a merely formal digitalisation, incapable of positively affecting system efficiency or the implementation of the rehabilitative function of punishment.