Returning to Cairo in 1490, Covilhã received two pieces of devastating news: Afonso de Paiva had died of plague. And second, two Portuguese Jewish agents (Rabbi Abraham of Beja and Joseph of Lamego) arrived with a message from King John II: "The sea route is being explored [Dias had reached the Indian Ocean]. Now find Prester John, for we have no other man who can do it."
Little is known of Covilhã’s early life, but records suggest he was born in Covilhã, Beira, around 1460. He entered royal service as a criado (retainer) and escudeiro (squire). His formative experience was serving under Don Pedro de Meneses, the governor of Ceuta (Portugal’s North African foothold), where he learned Arabic and the customs of the Maghreb. This service taught him that successful travel in the Islamic world required not just language, but an intimate understanding of Islamic law, commerce, and hospitality. By 1487, he spoke Castilian, Portuguese, Arabic, and some "native African" dialects. pedro da covilha
In 1487, while Bartolomeu Dias prepared to round the Cape of Good Hope, the King launched a simultaneous, secretive overland mission. He chose two men: Afonso de Paiva, a fluent Arabic speaker, and Pêro da Covilhã, a squire with a reputation for languages, loyalty, and an eidetic memory. Returning to Cairo in 1490, Covilhã received two
Initially honored, Covilhã was soon informed of the Ethiopian law of the guardians : no foreigner of value was allowed to leave, lest they reveal the kingdom’s weakness to hostile Muslims. He was given lands, a wife, and high office. He would never see Portugal again. He entered royal service as a criado (retainer)
Thus, Covilhã accepted his fate. He disguised himself as a Muslim cleric and traveled south from Massawa (modern Eritrea) into the highlands of Ethiopia. He was brought to the court of (or later, the Empress Dowager Eleni). The Ethiopians were amazed: here was a European Christian who spoke Arabic, knew the Bible, and could describe the world.