In the dynamic landscape of digital enterprises, cybersecurity has emerged as a critical determinant of organizational effectiveness. This study delves into the intricate realm of cybersecurity investment within ASEAN organizations, exploring the key facets that drive decision-making in this domain. Using a quantitative approach through structural equation modeling (SEM), we conducted an in-depth analysis based on a sample of 419 enterprises meeting cybersecurity criteria. Our findings reveal that cybersecurity strategy, financial considerations, and institutional and regulatory conditions are the primary factors influencing cybersecurity investments in the ASEAN region. In particular, financial resources emerged as the most critical determinant, underscoring the importance of adequate funding to address evolving cyber threats. Furthermore, our study highlights the crucial role of institutional and regulatory frameworks in shaping investment behavior, indicating a heightened awareness among firms regarding compliance with legal requirements. By unpacking these dynamics, our research provides deep insights into the intricate interplay of factors shaping cybersecurity investments in ASEAN organizations. This study contributes to the discourse by emphasizing the imperative nature of understanding the impact of risk aversion, organizational structures, and long-term practices on cybersecurity resilience. The implications of our findings extend to policy making, innovation, and future research directions in the cybersecurity domain, offering valuable insights to improve cybersecurity preparedness and resilience against evolving cyber threats.