The Disengagement Plan is the name assigned to the plan enacted in the summer of 2005 to evict all Israelis and military bases from Gaza Strip and four isolated settlements in northern Samaria and to withdraw unilaterally. The plan was controversial, yet it won the support of the majority of the cabinet and the Knesset members, as well as the support in Israel and the world. The eviction process of the residents was accompanied by vast activities of the army and police forces in fear of violent acts by the evacuees, and by extensive media coverage. It was one of the longest and most covered events in the history of Israel and intensified the conflict between security needs and free press. In democracies such as Israel, which faces security needs on permanent basis, the media are expected to carry social responsibility duties of not publishing information that is sensitive to national security. It is commonly agreed that although Israel is a democratic state where freedom of speech and freedom of the press are cornerstones of its existence, in all that relates to security things should be different, and security issues are above the need of the media to publish and the need of the public to know. The position of the press in the disengagement and the way they dealt with this dilemma are analyzed in this study based on covering reports in the main Israeli daily newspaper—Yediot Achronot—during the period from January 1, 2005 through August 24, 2005, when the evacuation of all Israelis from Gaza Strip was completed.