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When the Fortunate was damaged in a Nausicaan attack, Enterprise arrived to offer assistance with repairs. As the crews worked, Shaw and Fortunate executive officer Matthew Ryan hid from Captain Jonathan Archer the fact that they had a Nausicaan as a prisoner.
When Archer found out about the Nausicaan, he threatened to undo the repairs his crew had made to the Fortunate. Shaw would assist Ryan in trapping Archer and his officers in a cargo bay and detaching it from the ship.
While Archer and the others were being rescued by the Enterprise, Ryan and Shaw engaged the Nausicaan vessel that had attacked them earlier. Shaw was not happy with this action, but continued to follow his senior officer's orders. The Nausicaans returned fire and the Fortunate proved no match for the Nausicaan ships. The situation was only defused when the Enterprise intervened and negotiated a settlement: the return of the Nausicaan prisoner in exchange for allowing the Fortunate to leave without further incident. (ENT: "Fortunate Son")