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Introduction The increasing prevalence of diabetes and its associated complications presents a significant public health challenge, particularly in ageing populations. This qualitative study conducted in a healthcare setting in Singapore explored the lived experiences of patients with type 2 diabetes mellitus (T2DM) progression and complications, aiming to uncover challenges and enablers of effective self-care and complication management, thereby informing patient-centred policy and healthcare improvements.Methods A phenomenological approach was employed, involving one-to-one in-depth interviews with 13 participants with T2DM with complications. Participants were recruited through purposive sampling from the outpatient setting of a community-level diabetes care centre. Data were analysed through a reflexive thematic analysis.Results Seven themes emerged from the analysis: (1) pathways to initial diagnosis of diabetes, (2) diagnosis of diabetes-related complications (with subthemes of diagnosis in emergency and non-emergency settings), (3) barriers to help-seeking for complications, (4) barriers to diabetes complications management, (5) enablers of complications management, (6) experience of living with diabetes complications and (7) suggestions and recommendations for better care. Subthemes for barriers and enablers encompassed personal, healthcare-related and social/community factors. Findings revealed significant gaps in symptom recognition, treatment adherence and glycaemic control among participants. Despite these challenges, participants demonstrated considerable resilience and adaptability.Conclusion This study identified complex trajectories in T2DM progression, from the initial diagnosis to complication management, identifying key challenges and enablers. The findings highlighted the necessity for enhanced public education, tailored interventions and holistic care approaches. These insights have the potential to significantly improve the quality of life of individuals living with T2DM complications and alleviate the burden on healthcare systems, providing a foundation for future patient-centred diabetes management strategies.