During the tenure of captain Álvaro de Faria, in 1488, the Count of Borba Dom Vasco Coutinho distinguished himself in combat ahead of 70 horsemen against the qaid of Ksar el-Kebir, whom he personally fought and captured, despite having been ambushed.

A temporary truce was agreed upon with the Sultan of Fez, and while peace lasted, the villages in the vicinity of Asilah developed and cattle could be raised in safety.

In 1507 Meneses would lead a flotilla of three caravels to recon the harbours of Azemmour, Mamora, Salé and Larache accompanied by Duarte D'Armas, who produced sketches in preparation for future attacks.

As almost all the guns in the fortress were inactive, the Moroccoans managed to breach into the city on the second day of the siege, wound captain Dom Vasco with an arrow and force the Portuguese to seek refuge in to the citadel.

[13] As Dom Vasco informed King Manuel of the impending attack, he was provided with numerous reinforcements, and the Sultan was forced to withdraw shortly after arrived.

[13] The Portuguese built a stronghold, which was expanded and strengthened from 1509 onwards, with designs by Diogo de Boitaca, who rebuilt the citadel and the wall of its port, combining traditional architectural elements such as the keep and a sea-wall, with more modern ones, such as the bastions with embrasures.

[15] In 1520 Manuel I of Portugal opened a royal feitoria (trade post) in Arzila, for whose defense a coast-guard fleet called "Squadron of the Strait" was created.

The feitoria was provided with cloths, silks, headwear like caps, as well as lacquer, fine embroideries, semi-precious stones and spices which were highly sought after by Moroccan and Jewish merchants; Francisco Ribeiro was appointed as its first feitor, Tomé Pires as clerk, João Queimado as provedor and a branch was opened in Fez, the feitor of which was Francisco Gonçalves.

[18] Captain Dom João Coutinho took various measures meant to keep the city free from pestilence, such as turning back merchant caravans, forbidding raids, arresting anyone who challenged these rules, and forcing people to wash their clothes, however plague nevertheless broke out in January 12.

[19] Fearing for the safety of the stronghold, the alcaide-mor of Castro Marim and anadel-mor of crossbowmen Garcia de Melo sailed there in person with 600 men, among other volunteers from Portugal and Spain.

With the support of King John III, Coutinho signed a truce with qaid of Chefchaouen Muley Ibrahim on behalf of the Sultan of Fez Abu al-Abbas Ahmad ibn Muhammad, by a river the Portuguese identified as Rio Doce.

[21] On January 20, 1548, the captain of Asilah Dom Francisco Coutinho together with the captain of Portuguese Tangier Francisco Botelho raided the fields of "Alexarife" beyond Ksar el-Kebir, capturing more than 500 cattle and numerous POWs; upon trying to raid the region of Ksar el Kebir later that year, they were engaged by 400 horse and 1000 foot under the qaid of that city, however the Portuguese routed them killing over a hundred, and forced the remainder to seek refuge within the settlement.

[22] That same year, the qaids of Ksar el-Kebir, Tetouan and Chefchaouen together attempted to raid the fields around Asilah with a combined force of 2500 horse, however captain Dom Francisco Coutinho sallied out at the head of the garrison and put them to flight.

Fearing that the defenses of the city would be inadequate to resist the onslaught, King John III ordered Dom Francisco to speak to the inhabitants, register their belonging and oversee their evacuation to Tangier by sea, returning then to Portugal, while his successor Luís de Loureiro would stay behind with the soldiers and the frontiersmen to evacuate the objects, the artillery and demolish the church of São Bartolomeu as well as the Franciscan monastery.