Drone technology is applied in many domains to date, with clear societal benefits. Nevertheless, “the other side of the coin” concerns risks related to safety, privacy, accountability, and so on. Since we claim to be missing a sound and widely agreed-upon approach to tackle this problem, we are proposing our views accordingly, considering the context-awareness paradigm and its possible strengths with regard to drone technology. In this we are firstly addressing the challenge of maximizing the user-perceived effectiveness and the challenge of maintaining optimal system-internal processes; on top of that we are especially considering the external contextual factors, including rules, law-compliance, and public values. We are presenting just small illustrative examples and thorough validation of our proposed ideas is left for future research, since in the current paper we are reporting research-in-progress. Hence the contribution of the paper is two-fold – we not only align the context awareness paradigm to the drone technology application but we also make a special stress on the external contextual factors as claimed to be relevant with regard to the abovementioned problem.