Ramba uchiverenga ndima iyi - Pashure pokudzidza mutemo kwechinguvana, Woolsey akapinda muNavy somukuru mukuru wehondo musi waApril 9, 1800. Basa rake rokutanga raiva muchikepe chinonzi frigate, icho chaakashandisa kuenda kuWest Indies muna 1800 na1801. Akashanda kwenguva pfupi muHondo Yokutanga yeBarbary
pamberi chaipo pokuguma kwaro muna 1805. Muna 1807, Woolsey uyo akanga achangobva kukwidziridzwa pabasa akaudzwa kuti aende kuWashington, D.C., kwaakagadzira nzira yokutumira nayo mashoko kuNavy.