Climate change loss and damage (L&D) due to both sudden and slow-onset events are a growing concern for vulnerable countries. Over the last decade, agricultural communities in Fiji have suffered a range of serious L&D from severe drought events. Through a grounded theoretical lens, qualitative research was used to gain in-depth insights into L&D from droughts in the Fijian sugar industry. In-depth semi-structured interviews (n = 68) were conducted in two Indo-Fijian sugarcane communities, Barotu and Toko settlements in Western Viti Levu, Fiji, and with key stakeholders from government ministries, academia, and climate change experts at the national level. Purposive sampling was initially used to identify smallholder sugarcane farmers and key stakeholders. Theoretical sampling further identified key stakeholders for the interview. Despite implementing various adaptation measures, the Fijian sugar industry has suffered severe L&D, including non-economic L&D (NELD) and associated cascading effects. L&D included reduced yields, loss of crops, and reduced income. NELD included deterioration of mental, physical, and emotional health, loss of hope, and uncertainty. Cascading effects included increased food insecurity risks and impacts on children’s education. Key policy interventions are recommended, such as removing adaptation constraints, developing drought risk profiles and early warning systems, investing in livelihood diversification, and engaging in new markets to facilitate social and ecological transformations that will promote livelihood resilience.