Abstract: Military institutionalization involves internalizing military values, norms and structured behaviours that differ significantly from civilian life, leading to culture shock during the transition. Career experiences in the military imprint behaviours and identities that shape subsequent roles and how retired officers transition to the civilian world. The present study explored how military culture and identity influence military-to-civilian transition difficulty among retired army officers. Fourteen semi-structured interviews were conducted and analysed using interpretative phenomenological analysis, resulting in three overarching themes: Transition and Contrasting Cultures, Transition and the Role of Military Imprinting and Relearning-Connecting Disparate Cultures. The themes are divided into subthemes that shed light on how veterans navigate cultural disparities, experience identity and ego conflict tribulation and highlight factors that facilitate bridging the military-civilian cultural gap. The study's findings underscore the pivotal influence of military culture and the identity forged within military organizations on veterans' transition experiences. These insights carry significant implications for veterans and reintegration programs. It further offers possible suggestions to enhance transition interventions by addressing psychological distress related to reculturation and identity transition to facilitate smoother integration.