Serious games are games that are intended to serve a purpose other than merely to entertain, such as education or physical fitness. Childhood is a critical time for forming habits that extend into adulthood. Serious games can assist children in forming these habits while still being entertaining games to play. Additionally, virtual buddies can help both to motivate children to engage with the system and as a way to aid in forming these habits. With this in mind, we have designed several virtual buddy-based serious game systems to be used by children. These systems were designed with the ultimate goal of running them at a large-scale, unassisted in the field, where the environments played a pivotal role in the design and implementation of these systems. This article describes our experiences and lessons learned implementing each of these systems in the field. Finally, the goal of this dissertation is to analyze the data from our final study in order to uncover what parts of our latest system may affect participant engagement.