During the latter half of the 15th century, the Sultanate of Adal was marked by internal strife, resulting in a significant shift in power from the sultans to the Emirs and Imams. By the late 15th century, Emir Mahfuz emerged as a dominant leader, launching military campaigns against the Christian highland Kingdoms under Kings Eskindir and Na`od. His death in 1517 led to further power struggles until Imam Ahmad ibn-Ibrahim al-Ghazi, known as Gragn, rose to prominence in the early 1520s. Ahmad consolidated his power by resolving local conflicts and focusing on military campaigns against the Christian highland kingdom. In 1529, he achieved a decisive victory over King Libne Dingil at the Battle of Shimbra Kure with the help of a well-equipped army and Ottoman musketeers. By 1531, Ahmad had successfully annexed Dawaro and Bali and extended his control to the northern provinces, establishing his rule from Dembiya. His dominance continued until his defeat and death at the Battle of Woyna Dega in 1543.

The conflict between Adal and the Christian highland kingdom drew in Portuguese and Ottoman forces. In 1541, Portuguese troops led by Christovao da Gama arrived in Ethiopia but faced fierce resistance from Ahmad’s forces. Despite an initial defeat, Ahmad’s strategic errors and overstretched army eventually led to his defeat by the combined forces of King Gelawdewos and the Portuguese in 1543.

The prolonged conflict had significant consequences. It caused widespread destruction and loss of life, including the burning of churches and monasteries. The Christian highland kingdom’s power was severely weakened, and regional lords began to challenge royal authority. The conflict also triggered significant population movements, leading to increased ethnic and religious diversity in the region. Additionally, trade routes, especially the Zeyla trade routes, were severely disrupted, with trade not fully recovering until the 1560s.