The latest innovations in the field of electronics and telecommunications have revolutionised and brought new dimensions to human activities. As well as in other sectors, we observe that a wide range of electronic means have also shown their utility in criminal justice. Undergoing continuous development, these means ensure efficient monitoring of subjects and contribute to higher efficiency of judiciary systems, and provide “more humane” conditions compared with traditional incarceration for offenders when they execute criminal penalties. In this context, this study discussed the main challenges faced by Romania in implementing electronic monitoring (EM) devices in court proceedings and in the execution of criminal penalties. These have been researched from different perspectives, including those related to the current legal framework, opportunities provided by today’s developments in electronics, and in terms of financial public resources allocated for such purposes. Our study is among the few articles published on this topic and it brings to light both the advantages of introducing the Electronic Monitoring Information System (EMIS) in Romania, as well as the limitations, and overviews the international experience in this area by assessing the measures that have been taken so far worldwide to implement EMIS effectively. The final part of the paper presents the study conclusions, its limitations, and future lines of research.