Cultural institutions around the world are looking for ways to update their collections for the digital age. Today’s patrons, trustees, and donors demand new digital experiences. Art museums are especially hit due to the nature of their very not-digital displays. They all need the benefits of digital technology to survive, ensure the democratization of culture, keep open spaces for dialogue, and to allow for the free exchange of ideas and knowledge. However, museum system software can challenge even the best of them. Despite the challenges, there are still good reasons why institutions such as the Minneapolis Institution of Art (MIA) are finding success with their digital initiatives.