Automation has led to cost savings, increased safety, and efficiency, in high risk and complex systems such as the Nuclear Power Plant (NPP) Industry and medication dispensing process in hospitals. However, automation can also lead to critical risks and malfunctions due to a misunderstanding of the system and its automation, a mistrust of automation, or a lack of appropriate automation [2]. Knowledge about systems and automation will help human agents to document their situation awareness so they can understand system's complexity fully, and make decisions to ensure an appropriate systems' automation. This paper describes a diagnosis study based on our systemic approach to document medical operators' situation awareness about medication dispensing process functions, tasks, and risks, within both therapy management (care units) and logistic medication dispensing (pharmacy) circuits of drug dispensing process. Our methodology helps medical agents to document their situation awareness about major types of medication errors in unit care and pharmacy, and the allocation of automated and nonautomated solutions to control medication errors and malfunctions of drug dispensing process. It appears that automation can control 36% of identified medication errors in care units and 27% of identified medication errors in pharmacy. As automation is a non-self-sustaining leverage, they also have to secure their system with complementary human-based solutions. Automation systems have to be secured and reinforced by a relevant redeployment of freed medical agents in care units, to ensure full control of medication dispensing risks