Ceuta

The Marinids finally took Ceuta in 1387, with help from Aragon, but held it for barely a generation. On 21 August 1415 King John I of Portugal and his sons fell on the town with some 200 ships, and by nightfall it was theirs, the young Henry, later called the Navigator, among the wounded. The prize soon disappointed. The plunder fell short of the king's hopes, the caravan trade simply moved to Tangier, and Henry's attempt on that city in 1437 ended in disaster. Portugal kept Ceuta all the same, and in the 1540s enclosed it within the Royal Walls, with bastions and a navigable moat.

Sixty years under the Spanish crown from 1580 brought many settlers from Spain, and when Portugal broke away in 1640 Ceuta alone among its possessions stayed loyal to Madrid, a choice Lisbon accepted in 1668. The town soon had to defend that choice. From 1694 to 1727 the armies of Moulay Ismail besieged Ceuta for thirty-three years, the longest siege in history, and still the walls held.