Increases in access to information and communication technologies (ICTs) have given citizens new tools to organize politically. This development has particular importance for those living under authoritarian regimes that rely on the repression of free speech to maintain power. These repressitarian elites resort to a variety of means to establish (or re-establish) control over citizen online communications. However, it is counterproductive for countries to crack down too tightly on Internet expression, because such actions can create negative economic consequences for countries hoping to engage in the 21st century’s wired economy. The friction between online free expression and government repression is playing out with close interest of Western governments, human rights advocates, and citizens because it places many technology companies in the difficult position of either facilitating such government repression or finding themselves unable to compete in those markets. This chapter examines recent developments in Iran, Egypt, China, and Singapore. All four countries have been identified as having severe impediments to free expression. Iran and Egypt, however, have seen the rise of some organized opposition movements despite the controls on media expression, while China and Singapore offer useful case studies on the economic dimensions of the balance between participating in the global networked society and controlling citizen expression. This chapter considers how financial and economic factors lead to more moderate views of Internet use in those countries and examine the struggles between maintaining openness and crackdowns.