Inadequate intake of vitamin D is a global health issue related to severe diseases, mainly involving subjects with dark skin pigmentation, patients affected by malnutrition, malabsorption syndromes, or obesity, and elderly people. Some foods fortified with vitamin D have been tested in vivo, but fortification strategies with a global outreach are still lacking. This review is focused on food fortification with vitamin D, with the aim to collect information on (a) formulation strategies; (b) stability during processing and storage; and (c) in vitro bioaccessibility. Approaches to add vitamin D to various foods were analyzed, including the use of free vitamin D, vitamin D loaded in simple and double nanoemulsions, liposomes, casein micelles, and protein nanocapsules. Numerous studies were reviewed to elucidate the impact of food technologies on vitamin D’s stability, and mechanisms that lead to degradation were identified—namely, acid-catalyzed isomerization, radical-induced oxidation, and photo-oxidation. There is, however, a lack of kinetic data that allow for the prediction of vitamin D’s stability under industrial processing conditions. The roles that lipids, proteins, fibers, and antioxidants play in vitamin bioaccessibility have been clarified in various studies, while future needs include the design of specific food matrices that simultaneously achieve a balance between the long-term stability, bioaccessibility and, ultimately, in vivo functionality of vitamin D.