Digitalization has spread to affect many aspects of our lives but it has yet to fully engage equestrians. Many stables still extensively use the traditional whiteboard in combination with digital technologies. Is it because digital technologies are not designed with the unique needs of an equestrian? Since research in this area is lacking, this study describes the daily conventions around the traditional whiteboard and the complementary use of digital technology, while exploring equestrians’ attitudes toward digitalization. Ethnographic methods of participant observation and group interviews were conducted at two large equestrian centers in Sweden, and the informants were a mix of horse owners, stable owners, stable staff, and riding school students. The results show that whiteboards are used to communicate and collaborative planning, but there is a problem of not noticing new handwritten information. Informants are hesitant toward incorporating new digital technologies because they worry about limitations, and some are content with the current traditional conventions - even if they employ many workarounds to issues related to the traditional way. The study also contributes toward a broader understanding of how future digital technologies can be designed in the unique setting of a stable, and the importance of a thorough understanding of users.