This publication seeks to examine the concrete security challenges resulting from the cross-border exchanges between Benin and Nigeria. This border has received increased attention due to fears of a spread of Boko Haram activities towards the neighbouring countries as well as regionally operating transnational organized crime networks that are often associated with terrorist activities. Taking into account the cultural and geographic landscape of this border region, which represents a key transport route in the ECOWAS context, the nature of cross-border activities will be presented and their impact on security will be assessed. This paper argues that a more holistic approach is needed when designing border and security policies.