Since the 1990s, Islamic legal historians have explored fatwa collections as a vital source for social and cultural histories. However, the existing historiography on South and Southeast Asian Islamic traditions has largely ignored locally-produced fatwa collections, despite a considerable presence of such texts since premodern centuries. This paper focuses on a few such compilations from the sixteenth to eighteenth centuries in order to explore the juridical discourses and scholarly interconnections between the Shāfiʿī Muslims of the Indian Ocean littoral between Java, Sumatra, Malabar, Tamil Nadu, Hadramawt, Mecca and Cairo. These texts also help us understand the ways in which these oceanic Muslims engaged with their diverse everyday concerns when they endeavored to follow the ethical-cum-legal expectations of their religion. Many of their specific socio-political contexts, such as living amicably under a dominant non-Muslim polity and sharing the same social fabric with Hindus and Christians, were undiscussed in the hitherto legal texts of the Shāfiʿī school that were mostly written in the Middle East. The shared social dynamics became an increasing concern for jurists among them and they raised these issues to their colleagues and teachers elsewhere in the oceanic littoral. The issues varied from ritual purity to inter-religious marriages, extra-marital affairs leading to conversions, consumption of drugs, and disputes over permissible profit vis-à-vis forbidden interest. Taking up the juridical questions and answers related to love and lust, and trade and agriculture among these oceanic Muslims, I shall argue that the very act of questions was expressions of indigenous religious authority and deeper juridical debates, while the answers demonstrated an ongoing socio-cultural and economic continuum between the regions. The paper focuses on three fatwa compilations from sixteenth-century Malabar (Ajwibat al-Zabīdiyya li as’ilat al-Kālikutiyya or “Zabīdī Answers to Questions from Calicut”, Ajwibat al-Malaybāriyya or “Malabari Answers”, and marginally Ajwibat al-ʿajība ʿan al-asʾilat al-gharība, “Wonderous Answers to Rare Questions”), but it compares and connects them with similar works from Jāwī, Patani and Ḥaḍramī contexts where similar fatwas crisscrossed a wider Shāfiʿī cosmopolis of the Indian Ocean world.