Autocracies generally permit less freedom of expression than their democratic counterparts. The constraints on the free flow of information, however, are not fixed by regime type nor are they static within a given regime. One such example is Hosni Mubarak’s presidency in Egypt. During his time in office there were significant shifts in the media environment. In this paper, I explore shifts in the freedoms enjoyed by Egypt’s newspaper industry under Mubarak to explain the sources of this variation. During Mubarak’s presidency there were two periods in which private investors tried to break into the newspaper industry. First, in the 1990s investors incorporated media companies abroad and these companies printed newspapers in Egypt’s “Free Zones,” where many economic regulations did not apply, and sold them in the domestic market. This decade is known for the government’s heavy-handed attempts to curb the behavior of journalists, as a subset of the widespread repression experienced by civil society. By 1998 the Mubarak government closed the loophole that briefly enabled the entry of ‘Egyptian’ papers incorporated abroad. Then, starting in 2003, a new wave of privately-owned newspapers obtained licenses and markedly expanded the number of privately-owned daily and weekly publications available on Egyptian newsstands. Many of these publications gave considerable coverage to events ignored or buried by the state-owned newspapers, including cases of corruption, instances of religious tension and various protests events. I argue that the shifting response of the Mubarak regime to the flow of information can be explained by examining the relationship between the government and economic elites. In both periods examined in Egypt privately-owned newspapers enter the market, yet only in the later when economic elites have entered the government are these papers allowed the space to expand the content of the public sphere. When such an alliance exists, the old guard is less likely to feel threatened by the new outlets its allies establish because it understands that neither group benefits from rapid systemic change. Nonetheless, in such a context, the interests of the investors may be different enough from those of the old guard that the new publications do circulate information, both quantitatively and qualitatively, different from that which was previously available.