This study reports on a novel design methodology, namely, design-centered research (DCR), developed to analyze and evaluate the alignment between an online collaborative learning design and its enactment. The approach is illustrated in a study involving 40 groups in total. Twenty different online collaborative learning activities were designed and enacted by 20 groups of three students in each of two iterations. The collaborative learning design plans from the first round were adjusted after reflecting on misalignments observed through the method during the enactment, and then enacted and tested again by another 20 groups in the second round. The proposed method involves an interaction path graph as well as three proposed indicators of group functioning. These three indicators include: (a) the range of activated knowledge, (b) the degree of knowledge building, and (c) an interactivity of the approach. This approach to quantification of alignment between a collaborative learning design and its enactment was successful in revealing areas for improvement of the design. The results of the two round study indicate that the alignment significantly improved after the optimization of the collaborative learning design based on the analysis of the first round. The findings also suggest that optimizing a collaborative learning design using this method is associated with improvements in group performance. Building on these findings, the collaborative learning design framework is discussed in detail in this article, and resulting implications for practitioners are discussed in depth.