This chapter examines the most prominent milestones in the development of mass media in the Sultanate of Oman and the relationship between media and the political system as well as the legislative frameworks regulating media work in the Sultanate. At the end of this chapter, the author also discusses a number of challenges facing the Omani media, which are structural, legislative, and professional in nature. The author argues that the conditions and developments in the media industry globally and regionally seem to be conducive to bringing about fundamental changes in the media system in Oman, but those changes are totally linked to the political system’s desire and decision to make these changes.