Retirement is a major life transition, which leads to substantial changes across almost all aspects of day-to-day life. Although this transition has previously been seen as the normative marker for entry into older adulthood, its influence on later life has remained relatively unstudied in terms of technology use and cybersecurity behaviours. This is problematic as older adults are at particular risk of becoming victims of cyber-crime. This study aimed to investigate which factors associated with the retirement transition were likely to increase vulnerability to cyber-attack in a sample of 12 United Kingdom based older adults, all of whom had retired within the past 5 years. Semi-structured, one to one interviews were conducted and subsequently analysed using thematic analysis. Six themes were identified referring to areas of loss in: social interaction, finances, day-to-day routine, feelings of competence, sense of purpose, and technology support structures. We discuss the implications of these losses for building cyber-resilience in retirees, with suggestions for future research.