Abstract: This study explores the determinants, entry modes, and institutional challenges influencing Israeli and Jewish diaspora foreign direct investment (FDI) in the Republic of Cyprus through a qualitative analysis of 34 investor interviews and 10 external informants. Using Grounded Theory Methodology, the findings confirm the relevance of the OLI paradigm while identifying five emergent constructs—Regulatory Opportunism, Relational Asset-Seeking, Financial Arbitrage Advantage, Resilience-Seeking FDI, and Geopolitical Leverage. Entry modes are dominated by wholly owned subsidiaries, reflecting control imperatives, while obstacles such as bureaucratic inefficiencies and talent shortages persist. The study extends FDI theory by integrating institutional arbitrage and resilience logic, offering implications for policy and practice.