The development of dynamic covalent chemistry (DCC) sensors can fundamentally impact the disparate fields of biology, medicine, and materials science. At the heart of successful DCC-based sensors is a robust molecular recognition strategy that involves the binding of and the chemical or conformational response to the analyte. Recognition of molecule type is often comparatively simple to engineer since it relies on predicable functional group-specific reactions (e.g., nucleophilic attack of an alcohol on an iminium). In contrast, a difficulty of sensor design often stems from having to discriminate between different molecules bearing the same or similar functional groups or having to respond to specific analyte stereochemistry. Solving these types of challenges often involves creating sensors that recruit the subtle additive effects of modest (<2 kcal/mol) noncovalent interactions (NCIs). However, the development and understanding of these types of sensors is hampered by the difficulty of deconvoluting individual effects of the multiple, competing NCIs involved.