Cyber attacks by domestic and foreign threat actors are increasing in frequency and sophistication. Cyber adversaries exploit a cybersecurity skill/knowledge gap and an open society, undermining the information security/privacy of citizens and businesses and eroding trust in governments, thus threatening social and political stability. The use of open digital hacking technologies in ethical hacking in higher education and within broader society raises ethical, technical, social, and political challenges for liberal democracies. Programs teaching ethical hacking in higher education are steadily growing but there is a concern that teaching students hacking skills increases crime risk to society by drawing students toward criminal acts. A cybersecurity skill gap undermines the security/viability of business and government institutions. The thesis presents an examination of opportunities and risks involved in using AI powered intelligence gathering/surveillance technologies in ethical hacking teaching practices in Canada. Taking a qualitative exploratory case study approach, technoethical inquiry theory (Bunge-Luppicini) and Weick’s sensemaking model were applied as a sociotechnical theory (STEI-KW) to explore ethical hacking teaching practices in two Canadian universities. In-depth interviews with ethical hacking university experts, industry practitioners, and policy experts, and a document review were conducted. Findings pointed to a skill/knowledge gap in ethical hacking literature regarding the meanings, ethics, values, skills/knowledge, roles and responsibilities, and practices of ethical hacking and ethical hackers which underlies an identity and legitimacy crisis for professional ethical hacking practitioners; and a Teaching vs Practice cybersecurity skill gap in ethical hacking curricula. Two main S&T innovation risk mitigation initiatives were explored: An OSINT Analyst cybersecurity role and associated body of knowledge foundation framework as an interdisciplinary research area, and a networked centre of excellence of ethical hacking communities of practice as a knowledge management and governance/policy innovation approach focusing on the systematization and standardization of an ethical hacking body of knowledge.