Parents of children with special education needs and disabilities (SEN) often experience an intensified struggle to balance the risks of digital technologies while also embracing the opportunities. This chapter argues that, rather than being the exception, these families illustrate the dilemmas of the digital age felt in varying degrees by many families. For families with children with special education needs and disabilities, these dilemmas, we argue, are heightened given parents’ efforts to chart individualized pathways under conditions of significant uncertainty and reduced structural support. Digital technologies, in short, seem to suggest a potential path toward a socially sanctioned and innovative future, along with some creative workarounds to resolve a lack of domestic resources or capacity. However, the hopes raised by digital technologies for some of the families discussed in this chapter may be unrealized, and do not substitute for provision of better state services.