Digital transformation is among the most pervasive forces disrupting business models across every industrial sector. While prior research has explored the digital transformation of business models, the effect on the value proposition as a key element of the business model has received only limited attention. Drawing on an extensive single case study in the regional media industry involving 59 interviews with one service provider and its customers, this study explores the digital transformation of the provider’s value proposition and how this process was collectively enacted by the provider and its customers. This study develops an empirically grounded framework illustrating the key value proposition transformation drivers, provider and customer sense-making practices, and value element reshaping implications. Overall, this study advances contemporary digital transformation and value proposition research by demonstrating how the process of digital transformation changes the nature and content of the value proposition and how managers can facilitate this process.