Microscopic cracks in the cuticle (microcracks) are the first symptom of the strawberry fruit disorder ‘water soaking’ in which the fruit surface appears watery, translucent, and pale. Water soaking severely impacts fruit quality. The objective was to investigate the factors and mechanisms of cuticular microcracking in strawberry. Fluorescence microscopy revealed numerous microcracks in the achene depressions, on the rims between depressions and at the bases of trichomes. Microcracks in the achene depressions and on the rims were either parallel or transversely oriented relative to a radius drawn from the rim to the point of attachment of the achene. In the achene depression, the frequency of microcracks with parallel orientation decreased from the calyx end of the fruit, towards the fruit tip, while the frequency of those with transverse orientation remained constant. Most microcracks occurred above the periclinal cell walls of the epidermal cells. The long axes of the epidermal cells were primarily parallel-oriented. Microcracking increased during fruit development. Cuticle mass per fruit remained constant as fruit surface area increased but cuticle thickness decreased. When fruit developed under high relative humidity (RH) conditions, the cuticle had more microcracks than under low RH conditions. Exposing the fruit surface to increasing RHs, increased microcracking, especially above 75% RH. Liquid-phase water on the fruit surface was markedly more effective in inducing microcracking than high vapor-phase water (high RH). The results demonstrate that a combination of surface area growth strain and water exposure is causal in inducing microcracking of the strawberry cuticle.