This study concerns the experiences of Italian digital historians and their implications for historical scholarship. The present and future of the profession of historian, in academia and outside it, are inextricably linked to the digital revolution that is pervading society. This research brings to light some of the issues this connection between history and the digital has created in the Italian higher education environment and also the opportunities for resolving them, from the point of view of the minority of scholars who have worked and are working to develop this connection. Through grounded theory methodology and a set of in depth semi-structured interviews, the digital historians’ considerations, evaluations and strategies emerge and are organised and analysed in a conceptual framework that highlights focal points and critical junctures in the fields of research, education and professional development. The interviewees paint the picture of a passionate commitment to experimentation and innovation, set against a much bleaker background of complex institutional and professional relations that are not often conducive to productive, sustainable and well integrated digital historical scholarship. Keywords: Digital history, Digital humanities, Grounded theory, Digital scholarship, Higher education, Italy.