In December 1941, after the United States entered World War II, Jester was given a lieutenant's commission, and he was given command of the USCGC Icarus (WPC-110).

[8] Historians noted that, after sinking the U-boat, Jester had great difficulty getting instruction from his superiors as to whether or not he should rescue the crew.

He sought further instruction from the commandant of the Sixth Naval District, who ordered him to go back and rescue the survivors.

[11] On May 1, 1943, after he was allowed to speak to the press, The New York Times published two stories about his exploits, one of which was on its front page.

[12][13] On August 24, 1944, The New York Times reported that the destroyer escort on which Jester's son Maurice, a lieutenant, was serving, had also been credited with sinking a U-boat.