Soon after the War of 1812 began, Boyle took command of the privateer "Comet" and during his first cruise—conducted in the West Indies between 11 July and 7 October 1812—captured four vessels with an aggregate value of $400,000. On his second cruise, he sailed along the Brazilian coast, departing Baltimore on 25 November 1812. Though he made five captures, his second voyage was a financial disaster because British cruisers retook all five prizes. On 17 March 1813, Boyle slipped past the British blockade into Chesapeake Bay.