Occupational exposure to solar ultraviolet (UV) radiation is a recognized work-related risk, as is associated with the induction of long-term adverse health effects such as Non-Melanoma Skin Cancers and cataracts. Recent research provided new data suggesting an increased risk of specific forms of malignant melanoma, i.e., Lentigo Maligna Melanoma, for outdoor workers, while the relation of cumulative exposure to solar radiation with ocular diseases, such as uveal melanoma and macular degeneration, is still debated. Nowadays, one of the main focuses of prevention activities is the organization of multicomponent sun safety initiatives, which are proved to be effective, particularly when including technologies that are able to directly interact with individuals, such as phone apps, such as the recently released SunSmart Global UV App. Nevertheless, we should not forget that we are living in an era of profound changes, and phenomena such as climate change and the COVID-19 pandemic have an impact on all aspects of our lives, including how and when we perform, as well as the perception of, outdoor activities. In the future, this may result in possible changes in the scenario of occupational and leisure-time solar radiation exposure-related health risks.