Longevity of complex organic devices critically depends on the supramolecular integrity of the constituting layers and interfaces. Because the latter are soft matter they can structurally respond to perturbation of their supramolecular structure by relaxing back to a thermodynamically favourable state. To employ this response for self-healing optoelectronically active layers and particularly interfaces the degraded dyes in these layers need to be exchanged with non-degraded ones. Here, we present a dye-layer interfaced between a solid surface and a dye-reservoir that autonomously self-heals after photo-degradation of single molecules to restore its optical function. Surface sensitive in situ photothermal deflection spectroscopy reveals that this supramolecular self-healing approach critically depends on the thermodynamic stability of the layer, the chemical change of the dye upon degradation, and the medium dissolving the degraded dye and providing the reservoir dyes. Hence, the interplay of these parameters is key to successfully employ this supramolecular selfhealing approach to thin layers and interfaces in organic device for increased sustainability of organic optoelectronics and related fields.