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Programmers need documentation to comprehend software, but they often lack the time to write it. Thus, programmers must prioritize their documentation effort to ensure that sections of code important to program comprehension are thoroughly explained. In this paper, we explore the possibility of automatically prioritizing documentation effort. We performed two user studies to evaluate the effectiveness of static source code attributes and textual analysis of source code towards prioritizing documentation effort. The first study used open-source API Libraries while the second study was conducted using closed-source industrial software from ABB. Our findings suggest that static source code attributes are poor predictors of documentation effort priority, whereas textual analysis of source code consistently performed well as a predictor of documentation effort priority.