Although major settlements like Santiago de la Vega, now Spanish Town, were poorly defended and quickly occupied, resistance by escaped slaves, or Jamaican Maroons, continued in the interior.

[2] The expedition left England in December 1654, comprising a fleet of 17 warships and 20 transports, carrying 325 cannons, 1,145 seamen, and 1,830 troops (later reinforced by contingents from other English West Indian colonies to 8,000 strong).

[4] The fleet arrived in Barbados at the end of January 1655, and after two months of refitting, sailed for Hispaniola; on 13 April, Penn landed 4,000 men under Venables near Santo Domingo.

Wednesday the 10th our souldiers in numbers 7000 (the sea regiment being none of them) landed at the 3 forts...[7]At dawn on 21 May, Penn's fleet entered Caguaya Bay, which was extremely shallow.

There was an exchange of shots with the Spanish battery covering the inner anchorage, with resistance from a small number of settlers under Francisco de Proenza, a local estate owner, but they soon surrendered.

[9] Not all the Spanish accepted the English occupation; after evacuating noncombatants from northern Jamaica to Cuba, Proenza established his headquarters at the inland town of Guatibacoa.

After this, English governor Edward D'Oyley persuaded de Bolas to switch sides; without their support, Issasi finally accepted defeat, and fled to Cuba.