Cloud and Security are at the core of ‘Digital Underbelly’ – one of the most important tenets for empowering ‘Digital OneOffice’. AI for cybersecurity explores the use of AI to build sophisticated defence mechanisms against threats to enterprise data and systems. But, plans to apply AI for cybersecurity sometimes bring organizations to a ‘juncture of duality’, which refers to dependence of AI on real enterprise data that can prove to be a risk by itself while being shared with AI developers. In the December 2018 edition of HOLMES Advisory Board, the discussion delved deep into how AI can both aid and hinder cybersecurity. On one hand, AI can be used to identify fraudulent transactions, and on the other, it can also be used break the inbuilt security of a system. Organizations are realizing that instead of investing on cybersecurity in-house, they may maximize benefits by reformulating the business model and vendor/ partner relationships. An integrated solution approach ensures maximum business value while ensuring high defences against security threats. But more than any enterprise, the Governments across the world have the most important roles to play. Designing the regulatory frameworks and policies for data protection would aid enterprises in bringing in governance and guaranteeing ethical use of AI for cybersecurity.