Another influence on Prince Henry's behaviour was the search for knightly honour. Like many European courts of the time, chivalric traditions were very important. It was this moral and ethical code that governed practically all conduct and in which all achievement must be found. Under the influence of English chivalry, King Joćo introduced coats-of-arms, crests and mottoes for members of the Portuguese Court. For himself, the king chose the motto "Il me plaīt", "He pleases me". Following the king's lead, Prince Henry chose "Talent de bien faire", and it is unlikely that a more appropriate motto could be found. Talent did not mean power, nor did it mean faculty. Rather, it meant "desire". The desire to do well.

The search for knightly honour and Portugal's crusading legacy would combine to launch the Portuguese era of expansion. In 1411, King Joćo I concluded an uneasy peace with Castile that soon took the form of a non-aggression treaty which was specified to last for one hundred and one years, effectively making it impossible for Prince Henry and his brothers to win knightly honour in battle. The king proposed what he thought was an acceptable solution to the problem; Portugal would sponsor a jousting tournament with the best knights in Europe participating. Although the king thought that defeating these knights in such a contest would be enough to bring honour to his sons, the young princes were not convinced. Only battle could properly endow greatness. Prince Henry and his brothers began to think of an alternate plan that would enable them to win their spurs in a time of peace with the Castilians and the Spaniards. The city of Ceuta, which lay nearly opposite Gibraltar, presented a unique opportunity. The North African port served as the launching point for pirates operating in the straits, and was the port where many Christian prisoners began their tenure as slaves. Prince Henry organised an invasion force and when Portuguese ships, under the command of King Joćo I, entered Ceuta in 1415, the city was unprepared and fell to the Portuguese with relative ease.

The capture of Ceuta by Portuguese troops quenched Prince Henry's passion for warfare and was the launching point for Prince Henry's intellectual curiosity about exploration. He had witnessed the African coast firsthand, and the more he heard from prisoners, the more he was intrigued by this vast land.

Europe's exploration of the outside world began a new era of political, economic, and social contacts and it can certainly be argued that the voyages undertaken in Prince Henry's name marked the first sustained expansion outside Europe and set the tone for subsequent voyages. It can also be said that, by 1500, the Portuguese and Spanish overseas empires had finally exceeded the achievements of classical Greece and Rome. A definitive evaluation of Prince Henry's contribution to the rise of the powers, however, remains elusive. Was Prince Henry a skilful leader able to inspire those under his charge to greater feats of courage and nautical daring, or was he simply an administrator claiming credit for the accomplishments of others?