Gibraltar occupied a strategic position in the Middle Ages, serving as a gateway for armed forces from Morocco to enter the Iberian Peninsula.

[2] By the early 15th century, the Castilians had conquered much of Granada, but the Moors used Gibraltar as a secure base from which they raided the surrounding country.

[2] The Moors recovered Count Enrique's body and placed it in a barcina, or wicker basket, that they suspended from the castle wall.

[6] In August 1462, a Christian convert from Gibraltar passed word to the Castilians that a large part of the garrison had temporarily left the town.

He captured some Moorish soldiers and tortured them to gain information of the size of the garrison, which turned out to be too large for him to succeed with his own small forces.

To avoid coming to blows, it was agreed that the Duke and the Count of Arcos would enter the fortress at the same time and set up their banners simultaneously.

[12] A few years later, during an internal power struggle between Henry IV and a group of nobles supporting his brother Alfonso, the Duke of Medina Sidonia again besieged Gibraltar.