The purpose of the present investigation was to identify the relationship among different indicators of uncertainty that lead to potential item misalignment. The item-based indicators included ratings of ambiguity and cognitive complexity. The student-based indicators included (a) frequency of cognitive monitoring per item, (b) levels of misinterpretation per item, and (c) levels of lack of confidence per item. Results indicate that item cognitive complexity was related to all student-based indicators even after controlling for students' performance on the item. Moreover, item ambiguity was related to levels of item misinterpretation but not to frequency of student cognitive monitoring or lack of confidence. The implications of these conclusions for identifying item misalignment are discussed in light of construct-relevant and construct-irrelevant sources of ambiguity. (Contains 5 footnotes, 2 figures, and 5 tables.)