Implementation of the self-healing concept in coatings is challenging because they have to combine mechanical strength and chain mobility. This challenge is addressed in this work by studying the effect of the polymer microstructure on the mechanical properties and self-healing ability of waterborne poly(urethane-urea) coatings containing aromatic disulfide dynamic bonds. The structural modifications studied are the concentration and flexibility of the aromatic disulfide units and the effect of cross-linking. The effects and limits of these structural changes on the mechanical properties of the polymers and their healability were determined via a combination of DMA measurements, tensile tests, and rheological and scratch closure experiments. It was found that the flexibility of the disulfide unit was key to develop more efficient self-healing materials which offer the necessary molecular mobility for self-healing while simultaneously maintaining a level of mechanical strength that are essential for coating applications.