Digital Livestock Technologies (DLTs) can assist farmer decision-making and promise benefits to animal health and welfare. However, the extent to which they can help improve animal welfare is unclear. This study explores how DLTs may impact farm management and animal welfare by promoting learning, using the concept of boundary objects. Boundary objects may be interpreted differently by different social worlds but are robust enough to share a common identity across them. They facilitate communication around a common issue, allowing stakeholders to collaborate and co-learn. The type of learning generated may impact management and welfare differently. For example, it may help improve existing strategies (single-loop learning), or initiate reflection on how these strategies were framed initially (double-loop learning). This study focuses on two case studies, during which two DLTs were developed and tested on farms. In-depth, semi-structured interviews were conducted with stakeholders involved in the case studies (n = 31), and the results of a separate survey were used to complement our findings. Findings support the important potential of DLTs to help enhance animal welfare, although the impacts vary between technologies. In both case studies, DLTs facilitated discussions between stakeholders, and whilst both promoted improved management strategies, one also promoted deeper reflection on the importance of animal emotional well-being and on providing opportunities for positive animal welfare. If DLTs are to make significant improvements to animal welfare, greater priority should be given to DLTs that promote a greater understanding of the dimensions of animal welfare and a reframing of values and beliefs with respect to the importance of animals’ well-being.