Organizational research suggests that products whose categorization is ambiguous are more difficult for audiences to understand and thus receive lower evaluations. The present study aims to show that this relationship depends on context: while ambiguous products can be difficult to cognitively process, their experience becomes easier after exposure to other products that are conceptually related, especially if they are also ambiguous. In this context, the negative effect of ambiguity weakens as a result of greater cognitive fluency. An analysis of music consumers’ listening behavior on streaming and on-demand music platforms supports this argument.