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In 2349, Chao was the operations officer on the USS Rutledge, during which time Chao and Miles O'Brien were in a relationship. O'Brien and Chao ended their relationship, but were reunited in 2367 after Benjamin Maxwell attacked Cardassian targets. Chao, now the first officer of the USS Phoenix under Maxwell, was told by the captain that Starfleet had authorized their tactics. Chao thought it strange but did not question Maxwell and resigned her Starfleet commission soon after, despite Starfleet Command intending to promote her to captain and give her command of the Phoenix. (DS9 novel: Force and Motion)