Background: The victimization of children has been a prevalent issue long before the emergence of social media. The rapid development of the world wide web during the last decades has created more ways to get access to anyone anywhere at any time. This has brought along a yearly increase in the number of children who are abused online with the help of technological devices. So far, the existing research in the field of online grooming has been limited and especially in Estonia. Although the problem has been acknowledged, little is known about the offenders and how they target children for sexual purposes. Aim: The thesis aims to create a fuller picture of different types of online offenders in Estonia by using typology formed by the European Online Grooming Project. Furthermore, it looks into the rational choice processes of these offenders and how they establish a connection with their victims for personal sexual gratification while minimizing their risk of getting caught. Method: The data consists of 13 court cases of offenders who were found guilty in 2017-2022. The documents were accessed in Estonian Harju County Court and analyzed using thematic analysis. Results: The results showed that the most common types of online offenders in Estonia are intimacy-seeking and adaptable. The findings add support to previous research, showing that most online offenders use different controlling tactics like emotional abuse, threatening, blackmailing, and flattery to benefit their chances of gaining sexual gratification from the relationship. To minimize their chances of getting caught, the offenders had chosen vulnerable victims, faked details about their personal information, used different social media applications to their own benefit, and consistently asked the victims about their surrounding environment. Conclusion: The findings of the study are in line with previous research about the typologies and strategies of online groomers whilst providing new data for future research on the topic. The hope is that with a deeper analysis of the groomers behavior, the study helps to create further preventative measures to decrease the number of potential future victims.