This paper explores evaluation strategies to gauge the impact of a novel instructional design on international community participation online. This is done by conceptualizing and devising indicators for measuring "engagement" online amongst marginalized adult communities worldwide. In doing so, a review of online evaluation literature is conducted. In comparing dialogue sessions based on an ongoing traditional model to the new instructional approach, various challenges are faced in "measuring" asynchronous discussion. While the initial findings of marginal increase in engagement with the adapted instructional approach is not sufficient to prove that the new model works, this paper demonstrates various strategies challenges in evaluating dialectic engagement.