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Mobile use proliferation and the change from voice-only communications towards mobile multimedia contents is a reality. The emerging mobile multimedia technologies combined with the advances in local-based solutions open innumerable opportunities to offer intelligent infotainment services of mobile multimedia contextualized contents provision. The aim of the work described in this paper is to explore such possibilities through the development of a platform for providing on demand contents using mobile terminals. The paper concludes with the migration of this platform to a mobility environment (transportation scenario) where the context of the user could be considered (location, desired destination, preferences.) in order to know which contents have to be provided in a proactive way. The result is an innovative platform for the proactive delivery of mobile multimedia contents contextualized to the user profile with large applications in the entertainment and tourist industry.