Problems related to the environment are increasingly commonly known and consequently also technology is adapting to find suitable solutions. The ancestral technique of crop rotation was identified as a solution to address the problems related to pollution due to intensive food production (i.e. using fertilizers and pesticides). To ensure that this technique can actually improve food production, it is necessary to under- stand how modern technologies can support it; in particular the analysis of crop rotation can support farmers in decision making process and the optimization of farm management practices. The aim of this paper is to investigate how predictive process monitoring techniques can enhance crop rotation strategies by leveraging Agriculture 4.0 through real-time monitoring, resulting in more accurate and adaptive strategies. It is a position paper that proposes research questions for further study, which may help to develop the research area.