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In 2374 Corat Damar, second-in-command of the Cardassian Union forces occupying Deep Space 9, discovered a way to disable the minefield that the USS Defiant had laid over the mouth of the Bajoran wormhole in late 2373, and requested Dominion reinforcements from the Gamma Quadrant. Kar'ukan was placed as First to the Vorta Loriss, in command of 2,800 warships. The minefield was successfully destroyed and the Defiant, lead vessel of Operation Return, was forced to travel into the wormhole to confront the reinforcements.
Captain Benjamin Sisko was prepared to die fighting a holding action, but the Prophets inhabiting the wormhole stopped their Emissary to ask why. Sisko convinced them to interfere to protect Bajor and the entire fleet, including Kar'ukan, vanished. (DS9 episode & novelization: Sacrifice of Angels; ST video game: Star Trek Online)
35 years later, Deep Space 9, now under the command of Captain James Kurland, was hosting an international summit between the Federation, the Klingon Empire, the Cardassian Union, and the Deferi on the mounting Borg threat when all Hell broke loose. Kar'ukan's forces emerged from the wormhole and attacked the vessels surrounding Deep Space 9. Most of the station residents and the attending ambassadors were able to evacuate, but Kar'ukan beamed directly into the Operations center to secure it and killed the station's first officer, Commander Karen Andrews, with a blow to the back from his kar'takin. Loriss followed him aboard and claimed the station for the Dominion. (STO mission: "Second Wave")
After discovering that Kar'ukan and his forces had been time-shifted, the Alpha Quadrant forces managed to infiltrate a shuttlecraft past the Jem'Hadar and through the wormhole to contact the Dominion and convince them to order Loriss and Kar'ukan to stand down. Eraun agreed in exchange for the Federation releasing the female Changeling, and a starship traveled to Facility 4028 to retrieve her. Kar'ukan followed and told the Founder that he was prepared to carry the war throughout the quadrant, but she responded that he had failed her and would not get another chance. In a rage he ordered his Jem'Hadar to kill everyone in the facility except the Founder, but she, Eraun, and the starship's captain were able to exfiltrate successfully. (STO missions: "Operation Gamma", "Facility 4028")
The starship met Eraun's Vessel 6474 near Deep Space 9 and the Founder told Loriss to order Kar'ukan to stand down. Kar'ukan refused, seeking to reclaim his honor in battle. The captain was forced to infiltrate the station by spacewalk and badly wounded Kar'ukan in a brief firefight in Ops. Kar'ukan escaped to his flagship, a Jem'Hadar dreadnought carrier, and began to direct his Jem'Hadar against the attacking Starfleet ships. The battle began to turn in Kar'ukan's favor due to sheer weight of numbers, but the sudden arrival of the newly launched USS Enterprise-F under the command of Captain Va'Kel Shon turned the tide and Kar'ukan's flagship was destroyed with all hands. The surviving Jem'Hadar surrendered to the Founder's authority and returned to the Gamma Quadrant. (STO mission: "Boldly They Rode")
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