This study explores elements of difficult, complex transitions in an important contemporary context that have not been previously researched; findings could have wider potential implications for supporting learning practices. Lessons learned from an evaluation of digital technology use among groups of young people who are not in education, employment or training (NEET) will be deployed in another context, enhanced by additional approaches with another group of people who often need support during a difficult transition; that is, members of the Armed Services returning to civilian life.