Lentil (Lens culinaris Medik.) production faces challenges due to shifting environmental conditions, potentially leading to a transition towards cooler or highland Mediterranean environments. This study assessed the responses of five lentil genotypes across five diverse locations (L1–L5) managed under organic cropping systems over two seasons, focusing on key parameters including seed yield (SY), crude protein (CP), cooking time (CT), seed loss percentage (SL), and yield loss per hectare (YL) caused by bruchid (Bruchus sp.). Excessive seasonal rainfall (500 mm), low winter temperatures (−17.9 °C), bruchid SL, and spring sowing were identified as crucial, particularly in challenging environments like highlands. Genotype selection was highlighted as essential for balancing yield and stability, with the small-seeded cultivar ‘Dimitra’ demonstrating lower YL due to bruchid. Additionally, increased CP was noted in response to heightened bruchid infestations. Specific recommendations were proposed for different environments: In productive lowland areas with low bruchid pressure and high CTs (L1), prioritizing cultivars like ‘Samos’, ‘Dimitra’, and ‘Thessalia’ enhances quality. Locations with high bruchid populations (L4) were not favored organic production but can serve as genetic resistance screening sites. High-elevation environments (L3, L5) proved significantly less productive, underscoring the requirement for earlier and winter-hardy cultivars. These insights guide lentil cultivation, emphasizing the need for tailored breeding strategies adaptable to changing environments.