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Closed‐loop recycling of polymers represents the key technology to convert plastic waste in a sustainable fashion. Efficient chemical recycling and upcycling strategies are thus highly sought‐after to establish a circular plastic economy. Here, we present the selective chemical depolymerization of polycarbonate by employing a vanillin derivative as bio‐based feedstock. The resulting di‐vanillin carbonate monomer was used in combination with various amines to construct a library of reprocessable poly(imine‐carbonate)s, which show tailor‐made thermal and mechanical properties. These novel poly(imine‐carbonate)s exhibit excellent recyclability under acidic and energy‐efficient conditions. This allows the recovery of monomers in high yields and purity for immediate reuse, even when mixed with various commodity plastics. This work provides exciting new insights in the design of bio‐based circular polymers produced by upcycling of plastic waste with minimal environmental impact. [ABSTRACT FROM AUTHOR]