A facility is provided for automatically exchanging, via mobile ad hoc network transfer, a file between mobile devices based on derived user preferences and context. The facility includes monitoring use of one or more files received on a mobile device. Contextual user preferences are derived for one or more future automated file transfers to the mobile device based on the monitoring. A contextual user preference request is sent from the mobile device to an other mobile device based, at least in part, on the other mobile device being within mobile ad hoc network transfer range of the mobile device. The contextual user preference request asks that at least one file on the other mobile device related to at least one of the contextual user preferences be automatically transferred to the mobile device using mobile ad hoc network transfer.