Some journalists who cover conflict in countries like Syria, Ukraine, and Egypt work as freelancers. As opposed to full-time staff members of media organizations, freelancers pay for their own travel, security, drivers, and insurance. While this model of conflict coverage is financially beneficial for media organizations, freelancers indicate that they work for themselves in order to have “freedom” to make their own decisions about conflict coverage. The researcher studied the phenomena of freelance journalism in conflict scenarios through an exploratory study utilizing long interviews, an interpretative, textual analysis of war correspondents’ autobiographies, an online, open-ended questionnaire, and follow-up in-depth interviews with freelancers. This data was examined through the lenses of the Hierarchy of Influences model as well as Gatekeeping Theory. Findings show that media worker influences, media routine influences, as well as extra-media influences are perceived by freelancers to have strong influences on their coverage of conflict. These levels of the Hierarchy of Influences model are manifested through financial and safety. Freelancers also perceived that their gender influences conflict coverage because of cultural norms that dictate their access to sources. Finally, freelancers see the gatekeeping process as control that overlaps between the media worker, media organizations, and extra-media influences.