In the early fourteenth century, Guardamar was a modest place, home to around a thousand people, perched at the southern edge of the Kingdom of Valencia where the Crown of Aragon met Muslim territory. Frontier towns like this lived on borrowed calm. The council knew its defenses were inadequate and said so to the crown in writing, hoping money and men might follow. Neither arrived in time. For a generation the letter sat as an unheeded prophecy, while larger events gathered far to the west and southwest, in a long contest that would eventually reach this quiet corner of the Segura.

Guardamar's fall belonged to the Battle of the Strait, the decades-long struggle among Castile, Aragon, Portugal, the Emirate of Granada, and the Marinid dynasty of Morocco for control of the passage between the Mediterranean and the Atlantic. In 1329 the Granadans recovered Algeciras. In 1330 Pope John XXII granted the Christian kings three years of church tithes on the condition that they campaign in person against Granada. Castile's king Alfonso XI marched, but on 19 February 1331 he signed a truce, and that truce freed the Granadans to turn elsewhere. They massed a force reported at five thousand horsemen and fifteen thousand on foot, among them five thousand crossbowmen, under the command of Abu-l-Nuaym Ridwan ibn Abd Allah, and pointed it at the border of the Crown of Aragon.

As the danger became clear, the people of Guardamar sent for help to the royal official Guillem de Liminyana, who was at Orihuela. What came was almost nothing: a single commander, Pere de Tona, with twenty-seven crossbowmen and lancers. The main army entered the Kingdom of Valencia by way of Orihuela, and on 18 October 1331 the siege closed around the town. It did not last. The next day Guardamar was overrun and taken completely. Twenty-two of its defenders were killed, and the survivors, soldiers and townspeople alike, were carried off as captives, torn from homes their council had begged the crown to protect. The prophecy on paper had come true in the space of a single autumn morning.

The victors did not linger. Reinforced by the Marinids from Morocco, the Granadan army moved on to besiege and take Gibraltar, the greater prize on the strait itself. Guardamar's loss was one small wound in a much wider war. The Christian powers regrouped in their turn: in 1333, a coalition that included the commander of the Order of Montesa, the writer-prince Don Juan Manuel, and the bishop of Murcia agreed to strike back into Muslim land. For the ordinary people of Guardamar, though, the grand strategy meant little. They had lived on a fault line between empires, warned their king, waited, and paid the price when the ground finally shifted beneath them.