This chapter looks at the status of the freedom of the press, and the legal possibilities and obstacles that affect media’s ability to hold power to account and safeguard the principles of democracy. The legal environment in countries as diverse as the United States, Egypt, and Sweden differs greatly, and affects the ability of journalists to report news to citizens that enables them to take part in the public discourse, based on theories on the public sphere. And according to theories on democracy, informed citizens can be seen as a requirement for democracy. Thus, certain conditions are necessary for journalism to be considered the fourth estate, and arguments for this are based on comparing the working conditions for independent professional journalists by semi-structured interviews with local journalists. Aspects discussed are access to official documents, media’s right to protect anonymous sources and the increase in intimidatory tactics against reporters, as the three countries are in different ways applying laws in order to regulate the media and their ability to hold power to account.