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It was created on Stardate 119603 by the Executive Council and was awarded individuals who showed conspicuous heroism in the defense of the Federation worlds and people during times of conflict. It was named in honor of a successful Starfleet Marines defense of the planet Karag against Klingon attackers during the Four Years War. The Karagite Order of Heroism appeared as a stylized humanoid female with outstretched arms which were grasping of an upraised sword that was attached to scarlet and white horizontal stripes.
Lieutenant Asham Razi of the USS Hood received the medal on Stardate 3/0003.17 for the successful capture of a previously unknown pirate base on the planet Gibraltar. (FASA RPG modules: The Four Years War, Star Trek: The Next Generation Officer's Manual)
Captain James T. Kirk also accepted this chivalric honor from Starfleet in the mid 23rd century prior to his court martial. (TOS episode: "Court Martial" ; ST - The Lost Era novel: Serpents Among the Ruins)