During the winter, Grenville was granted a waiver to lead a fleet into the Caribbean to attack the Spanish, and White was permitted to accompany him in a resupply ship. The fleet was set to launch in March 1588, but unfavorable winds kept them in port until Grenville received new orders to stay and defend England. Two of the smaller ships in Grenville's fleet, the "Brave" and the "Roe", were deemed unsuitable for combat, and White was permitted to take them to Roanoke. The ships departed on April 22, but the captains of the ships attempted to capture several Spanish ships on the outward-bound voyage (in order to improve their profits). On May 6 they were attacked by French mariners, (or pirates), near Morocco. Nearly two dozen of the crew were killed, and the supplies bound for Roanoke were looted, leaving the ships to return to England.