Assistive technologies, as most recently enhanced by artificial intelligence, are increasingly used by persons with disabilities to express their will. However, the current legal framework does not always allow the use of technological tools for the conclusion of valid legal transactions. More specifically, in this contribution, attention will be focused on the analysis of the rules governing succession law in order to show how the rigid testamentary formalism that characterizes our legal system is an obstacle to the finalization of a valid will by those who can only express themselves by means of technological devices. The social repercussions, from the perspective of organizational studies, of the contradictions arising from the lack of coordination between technological development, the legal framework and the specific needs of people with disabilities will also be examined.