When the count was in Santarém, the king was advised to advance on Alcántara and ordered the count to go to the Alentejo and assemble the men from that region and those from the kingdom of the Algarve to accompany him to Alcántara.

The count went to Évora to gather his men, as the king had ordered him. From there, he set off for Alcántara. Along the way, he joined the king, who had left Santarém by a different route, along the bank of the Tagus, following it upstream and crossing over a pontoon bridge of boats that he had ordered to be made strong and very well constructed. The gathering took place at a brook situated this side of Crato, called Cafardela. From that place, the constable always advanced in the vanguard and the king in the rearguard with the Masters of Christ and of Santiago and other lords and noblemen, along with many men, who amounted to about 4,000 lances, plus a large number of foot soldiers and crossbowmen. With them went many wagons with siege engines, as well as scaling ladders and provisions. They went through Crato, then through Meadas and Valencia [de Alcántara]; and on a Saturday they launched an attack on Alcántara – this was in the month of May 1401.

The king had ordered the pontoon bridge over which he had passed to be brought to him so that he could cross over the Tagus in order to set up a camp on the far side of the river, which flows round that side of the town, and another [camp] on the near side, so that the town would be totally surrounded. With the camp set up on the near side, the king ordered his siege engines to be armed and to fire on the town but, waiting each day for the pontoon bridge, he became very concerned because it was late in arriving. While the ladder was being repaired and a few days went by, the king sought counsel on whom to send out for forage, on account of the rumours about the many [Castilian] troops that were said to be around that region with the aim of helping the besieged town.