Objectives: Military retirement happens early in the lifespan presenting a unique transition that challenges chronic illness. The purpose of this study was to explore the factors that military retirees experience as they transition from active duty to military retirement that they perceive as inhibiting their ability to manage type 2 diabetes (T2DM) or pre-diabetes (preDM) and/or which increase their disease risk. Methods: Twenty veterans diagnosed with T2DM or preDM participated in semi-structured, face-to-face interviews in a private setting at their primary care clinic. Transcripts were analysed using constant comparative method. Participants were aged 44 to 63 (M=56), with 15 diagnosed with T2DM and 5 as preDM. They had been retired from the military 6 to 22 years (M=14years). Results: Participants linked five inter-related challenging factors to their T2DM/preDM diagnosis (when diagnosed post-retirement) and/or to their inability to manage their disease: (1) diet/eating habits, (2) physical activity, (3) weight fluctuation, (4) health care interactions and (5) systematic barriers. Military retirees' experiences were embedded within a 'cultural shift'. They struggled to maintain self-management behaviours once they were no longer on active duty and had more independence as civilians. Discussion: Results provide support for diabetes education during military retirement. Military retirees need help maintaining healthy lifestyle behaviours beyond the structured, health-focused military culture. They could also benefit from patient-provider communication skills training in navigating systematic barriers and attaining the support needed to manage their disease. [Additional funding for this study came from research and development award, 59th MDW/ST 6.3.]