This paper presents the design, implementation and validation of an enhanced mobile phone messaging system (DeDe), allowing the sender to define the context in which the message will be delivered to the recipient. A field trial among a socially tight group of teenagers showed that the DeDe feature was incorporated as part of the participants' existing messaging culture. 11,4% of their total messaging output made use of the DeDe feature. The most frequently used context parameters were location (based on network cell-ID) and time. Novel message practices emerged, as compared to `normal' messaging, both in terms of timing of message sending, as well as creating content that specifically exploited the DeDe feature. Some use barriers were recognized, the most important being the sender's uncertainty of delivery success. Implications for design are discussed. Author Keywords Mobile messaging, location-based messaging, field trial, context, mediated communication. ACM Classif...