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The properties of basic arithmetic operations are an important subject in elementary math education as tools for arithmetic computation and for promoting early algebra, and are systematically emphasized by the Common Core State Standards. However, the teaching of these properties is often challenging for teachers and students alike. This paper investigates the teaching of the associative property of addition and multiplication in a “natural” classroom setting, seeking to identify both challenges and successful teaching strategies as they occur in actual instruction. Many teachers were found to struggle with disambiguating the associative and commutative properties, and with adequately linking abstract use of the associative property to concrete reasoning – however, some demonstrated successful and rich concrete linking. Implications are discussed.