In response to the sudden proliferation of hobbyist unmanned aerial vehicles used for digital imaging – or “drones”, as they are popularly, but rather inaccurately, labelled – the Singapore government enacted the Unmanned Aircraft (Public Safety and Security) Act in 2015 and also amended various existing laws relating to air navigation. However, in view of the rapid evolution in drone technology and the ever-expanding range of useful applications brought about by drones, what are some of the challenges that would be faced when enforcing the law against recreational users of aerial imaging in particular, and what are some of the changes that should be made to the law when the matter is revisited for review in the future? Through an appraisal of the current state of drone technology and a comparison with the rules that have been adopted in various other jurisdictions around the world, this article considers how our existing laws on recreational users of drones can be improved, and also highlights emerging issues that would eventually warrant regulatory attention here and elsewhere. The matters to be discussed here include whether limits should be placed on distance, speed, and people proximity, whether drones truly pose a threat to privacy and other related rights, and how drone safety can be enhanced independently of a permits and permissions system.