Artificial Intelligence (AI) technologies could be broadly categorised into Analytics and Autonomy. Analytics focuses on algorithms offering perception, comprehension, and projection of knowledge gleaned from sensorial data. Autonomy revolves around decision making, and influencing and shaping the environment through action production. A smart autonomous system (SAS) combines analytics and autonomy to understand, learn, decide and act autonomously. To be useful, SAS must be trusted and that requires testing. Lifelong learning of a SAS compounds the testing process. In the remote chance that it is possible to fully test and certify the system pre-release, which is theoretically an undecidable problem, it is near impossible to predict the future behaviours that these systems, alone or collectively, will exhibit. While it may be feasible to severely restrict such systems\textquoteright \ learning abilities to limit the potential unpredictability of their behaviours, an undesirable consequence may be severely limiting their utility. In this paper, we propose the architecture for a watchdog AI (WAI) agent dedicated to lifelong functional testing of SAS. We further propose system specifications including a level of abstraction whereby humans shepherd a swarm of WAI agents to oversee an ecosystem made of humans and SAS. The discussion extends to the challenges, pros, and cons of the proposed concept.