This paper provides a study of an influential sixteenth century fatwa collection, al-Ajwibat al-ʿajībat ʿan al-asʾilat al-gharība, written by the Indian-Malabari Shāfiʿī scholar Zayn al-Dīn al-Makhdūm II (1531-1583). Al- Makhdūm II came from a prominent Hadrami family of religious notables originally from Ma‘bar in Yemen. Al- Makhdūm II worked primarily as a teacher in Ponnani and authored approximately ten books in the fields of Islamic law, theology and Sufism. Al- Makhdūm II is most famous for Fatḥ al-muʿīn bi sharḥ Qurrat al-‘ayn, an abridged version of Ibn Hajar’s Tuḥfat al-muḥtāj bi-sharḥ al-Minhāj, and for Tuḥfat al-mujāhidīn fī baʿḍ akhbār al-Burtughālīyīn, a call for jihad against the Portuguese presence. His legal works were influential across the Indian Ocean world, including in Indonesia, Sri Lanka, and East Africa. They continue to be taught in many Islamic seminaries, especially those committed to the Shāfiʿī school of law. The legal works of Zayn al-Dīn al-Makhdūm II have been read as evidence of a process of localization or indigenization of Islam in Malabar which some scholars have described as “Monsoon Islam”. These claims have been based primarily on a reading of Fatḥ al-muʿīn. In this presentation, I focus instead on the largely neglected al-Ajwibat, one of the two fatwa collections authored by Al- Makhdūm II. Al-Ajwibat contains 177 questions and answers on issues ranging from ritual questions, family and commerce to interfaith relations and political engagement. The questions were asked by al-Makhdūm II to ten of his Shāfiʿī teachers in the Hijaz, Cairo, and Hadramawt. In this paper I examine how the answers confirm or deviate from central Shāfiʿī legal positions by comparing the fatwas in Al-Ajwibat to those found in the legal manuals of Yaḥyā ibn Sharaf al-Nawawī (1233-1277) and Ibn Hajar al-Haytamī (1503-1566). I focus specifically on fatwas that pertain to local customs and political pluralism. What is the legitimacy of Malabari linguistic conventions in ritual practice and in marriage and divorce? How does non-Muslim rule shape conditions for the lawful appointment of a Muslim qāḍī? To what extent may inheritance rules be influenced by common practices in Malabar? I argue that these fatwas show the scope and limits of indigenization of Islamic law in the context of Malabar and shed light on some of the transformations taking place in the sixteenth century Indian Ocean world due to the emergence of European powers and changing relations between Muslims and Hindus in the subcontinent.