Attempts at reconstructing the nature and organizational structure of the Essene movement have largely been based on the manuscripts of the Damascus Document and the Rule of the Community. This article calls attention to a number of additional fragmentary documents from Cave 4, and examines the challenges they pose and how they relate to various theories regarding the nature of the communities behind them. A fundamental question is to what extent the so-called rule texts reflect actual historical circumstances, and this question is intrinsically linked to the question of the function of the texts in the communities that used them. A study of the organizational terms used in the documents reveals that these terms were used in a variety of ways, and while some terms may reflect actual historical circumstances, others probably did not. This result has implications for the feasibility of using these texts for historical reconstruction.