In this paper, we are addressing the relationship between ambiguity and obscurity by comparing political with literary use of language. In particular, we are considering contexts in which ambiguity, deriving from underspecification, is strategically used as a device to establish a certain degree of obscurity. We suggest that this strategy is based on an undeclared identification of meanings that are in fact distinct, thus creating false or at least misleading impressions. By contrast, we present literary strategies of ambiguity which also work with combinations of meanings. While the strategies share this combination, they differ vastly in purpose and effect. Our examples are taken from Boris Johnson’s 2021 »Levelling Up«-Speech as well as from poetry and plays by William Shakespeare. Their comparison proves to be particularly fruitful when it comes to conceptualising the ambiguities of »levelling (up)« and their uses in context.