In a collaborative effort between three departments at Portland State University, investigators designed and created Information Literacy (IL) modules tailored to the needs of Art History students utilizing two delivery platforms. One platform employed adaptive software (in this study, the product is called Realizeit), and the other was a static environment called Pressbooks. Students were randomly divided into cohorts based on these delivery methods. The author compared results of pre and post information literacy assessments and completed an analysis of students’ preliminary bibliographies to measure the success of the IL instruction. But the core investigation was to determine whether the same content delivered in different online learning environments were appreciably different in terms of students’ performance outcomes. This study reaffirms the value of information literacy instruction in Art History classes as evidenced by significant student improvements. Regarding the efficacy of adaptive learning software, however, the outcomes of this study are inconclusive.