As theory-based evaluation (TBE) engages in situations where multiple stakeholders help develop complex program theory about dynamic phenomena in politically contested settings, it becomes difficult to develop and use program theory without ambiguity. The purpose of this article is to explore ambiguity as a fruitful perspective that helps TBE face current challenges. Literatures in organization theory and political theory are consulted in order to cultivate the concept of ambiguity. Janus variables (which work in two ways) and other ambiguous aspects of program theories are classified and exemplified. Stances towards ambiguity are considered, as are concrete steps that TBE evaluators can take to identify and deal with ambiguity in TBE.