This paper showcases development on a digital learning environment built for users interested in ancient languages. The environment adopts a two-pronged approach: first, it assesses user progress during the language learning phase by using exercises such as treebanking and alignment; then, it offers users the opportunity to contribute their own annotated data. This paper provides a description of user testing conducted by the eLearning team in order to understand how these methods affect user engagement and persistence. The results of user testing showed higher user engagement and retention rates when compared to a more traditional quizzing method.