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The exploration of Africa occupied a great deal of Prince Henry's time and attention, a past conquest soon became a pressing issue. The Portuguese colony at Ceuta was rapidly becoming a drain on the national treasury and it was realised that without the city of Tangier, possession of Ceuta was worthless. When Ceuta was lost to the Portuguese, the camel caravans that were part of the overland trade routes began to use Tangier as their destination. This deprived Ceuta of the materials and goods that made it an attractive market and a vibrant trading locale, and the city rapidly became an isolated community. The cost of garrisoning generated further losses, a situation that might be reversed if Portugal were to capture Tangier. There was, however, another reason to launch a military campaign against Tangier. Prince Fernando, Prince Henry's youngest brother, was only eleven years old when the Portuguese captured Ceuta and he had not won his spurs in battle like his older brothers. After much prodding, and some court intrigue, Prince Henry managed to convince his brother to begin preparations for an attack on Tangier in 1436.
In stark contrast to the attack on Ceuta years before, the Portuguese assault on Tangier was poorly conceived and badly executed. When the Portuguese fleet set sail in August 1437, it contained only 6,000 troops; Portuguese planners originally estimated that it would take 14,000 soldiers to comprise an adequate striking force. Furthermore, no attempt was made by Prince Henry to disguise his intention to attack the city, and the North Africans were well prepared to turn back the Portuguese. Three times Prince Henry attempted to assault the city, and all three times his armies were repulsed. Only after his chaplain deserted him and told the North Africans the details of the new assault did the full measure of the futility of his attacks grip Prince Henry. Realising that his position was hopeless, Prince Henry asked the North African leader, Sala-ben-Sala, to dictate his terms for surrender. The North African's terms were decidedly harsh. Not only would the Portuguese have to agree to an exchange of hostages - Prince Henry's brother, Prince Fernando, for one of Sala-ben-Sala's sons - but the Portuguese would have to abandon the city of Ceuta. The exchange of hostages was a show of good faith easily agreed upon by the two leaders but it soon became clear that Sala-ben-Sala would have to wrestle Ceuta from the Portuguese. Sala-ben-Sala declared that the Portuguese would have to abandon Ceuta before Prince Fernando would be released. When the Portuguese protested, and reminded the North Africans that they were holding one of the king's sons, Sala-ben-Sala replied that he had many other sons and that he did not particularly care for the one the Portuguese were holding. Thus, Prince Henry had to make a decision, either he could sacrifice the city of Ceuta to obtain his brother's release, or he could keep Ceuta and condemn Fernando to imprisonment. The city of Ceuta was deemed to be an important outpost of Christianity against the infidel and even the Pope advised against trading Ceuta for Prince Fernando's life. The city could not be sacrificed for one man, even for the brother of the king of Portugal. Needless to say, Prince Fernando died in captivity four years later.