The current push towards increasingly digital ecosystems with the advent of Artificial Intelligence has challenged existing practices for risk and reliability analysis writ-large. Existing regulations are currently being scrutinized for applicability and ensuring a level of safety equivalence towards prior technology. One large push by multiple industries has been the significant investment into developing complex algorithms as assurance measures for AI-integrated cyber systems. Though useful, such approaches face challenges as the AI field is rapidly evolving in terms of architecture, infrastructure, and integration prospects. Instead, a potential starting point may be better focused on questioning the fundamentals of operability and functionality for such systems. This approach can provide risk-informed flexibility in engineering decision-making while maintaining a level of safety equivalency. This paper explores the differences between functionality and operability as it relates to varying technologies and the implication of AI as a dependent failure mode, rather than existing paradigms of independence. Finally, the implication of these results will be drawn to AI systems.