From a design perspective, the intentionality of students to engage in surface or deep learning is often experienced through prescribed activities and learning tasks. Educators understand that meaningful learning can be furthered through the structural and organizational design of the online environment that motivates the student towards task completion. However, learning engagement is unique for each student. It is dependent on both how students learn and their intentions for learning. Based on this challenge, the design of online discussions becomes a pedagogical means in developing students' intentionality for the adoption of strategies leading to deep learning. Through a Design-Based Research (DBR) approach, iterative design of online learning components for undergraduate field experience courses were studied. For this paper, the focus of the research is on examining factors that influenced deep and surface levels of learning in online discussion forums. The results indicate that design factors (i.e., student engagement, group structures, and organization) influence the nature and degree of deep learning. From the findings, two implications for practice are shared to inform the design and scaffolding of online discussion forums to foster deep approaches to student learning.