International trade involves crossing several organizational boundaries. This revelatory case study follows fresh cut roses’ journey from the growers in Kenya to the retail distribution in Holland and shows relatively high barriers related to the associated activities, information and documents, etc. Our empirical findings reveal the serious limitation that existing inter-organizational system (IOS) only facilitates actor-to-actor information forwarding in a communication chain of peer-to-peer communication along the supply chain and has no provision for persistent and simultaneous exchange of information between multiple actors. To address this limitation, we conducted a comparative analysis of affordances of the existing vs. future inter-organizational information systems with a focus on sharing critical information. Our extended analysis shows that modern IT features supporting affordances could be useful for the actors’ collaboration in the trade lane of the roses. We discuss some of the benefits of our proposed approach (e.g. lower transaction cost and real time information) but also raise some concerns (e.g. about trust and governance) which calls for further research.