Photomechanical crystals act as light‐driven material‐machines that can convert the energy carried by photons into kinetic energy via shape deformation or displacement, and this capability holds a paramount significance for the development of photoactuated devices. This transformation is usually attributed to anisotropic expansion or contraction of the unit cell engendered by light‐induced structural modifications that lead to accumulation and release of stress that generates a momentum, resulting in readily observable mechanical effects. Among the available photochemical processes, the photoinduced [2+2] and [4+4] are known for their robustness, predictability, amenability for control with molecular and supramolecular engineering approaches, and efficiency that has already been elevated to a proof‐of‐concept smart devices based on organic crystals. This article presents a summary of the recent research progress on photomechanical properties of organic and metal‐organic crystals where the mechanical effects are based on [2+2] and [4+4] cycloaddition reactions. It consolidates the current understating of the chemical strategies and structure–property correlations, and highlights the advantages and drawbacks of this class of adaptive crystals within the broader field of crystal adaptronics.