This chapter, based on the reviewed countries’ experiences, provides a comparative analysis of the day fines system in Europe. It seems that making the sentencing system more equal, and reducing short-term imprisonment, are common goals for countries to adopt day fines. Some countries can be rendered as a success in terms of the extent of implementing day fines and the ability to meet the desired goals. Nevertheless, as the experience of many other countries shows, there can be major challenges for day fines to be properly implemented. The main two challenges identified in this chapter are the complexity of calculating the fine, exacerbated by the frequent lack of guidelines, and a negative perception, derived mainly from lack of understanding of the system (by the public) and lack of support from the sentencers. In this chapter, we provide policy recommendations how to address these two specific challenges, as well as more general recommendations to expand the use of day fines. Given the multiple advantages day fines offer, it seems worth investing in its proper implementation. These recommendations may assist jurisdictions who already implement day fines, well as those interested in introducing this model into their criminal justice system