Essay scoring is a difficult and contentious business. The problem is exacerbated when there are no “right” answers for the essay prompts. This research developed a simple toolset for essay analysis by integrating a freely available Latent Dirichlet Allocation (LDA) implementation into a homegrown assessment assistant. The complexity of the essay assessment problem is demonstrated and illustrated with a representative collection of open-ended essays. This research also explores the use of “expert vectors” or “keyword essays” for maximizing the utility of LDA with small corpora. While, by itself, LDA appears insufficient for adequately scoring essays, it is quite capable of classifying responses to open-ended essay prompts and providing insight into the responses. This research also reports some trends that might be useful in scoring essays once more data is available. Some observations are made about these insights and a discussion of the use of LDA in qualitative assessment results in proposals that may assist other researchers in developing more complete essay assessment software.