At opposite ends of the Arabian Sea, on either end of the fifteenth century, two men wrote about why they decided to learn ṭibb. Ṭibb was a kind of elite medicine properly learned through both textual study and apprenticeship; those who had trained enough to be called physicians (ṭabīb) policed its boundaries carefully. But here, in Gujarat at the end of the fourteenth century and in Yemen in the late fifteenth, two pious men with little to no formal training charted strange pathways through ṭibb. This presentation will explore the regional specificities of Islam and of ṭibb that shaped these paths for Shihab al-Din Nagauri in Sultanate Gujarat and Ibrahim al-Azraq in Rasulid Yemen. Nagauri's Sufi teacher had as much to do with his turn toward ṭibb as al-Azraq's Shafi'i shaykh, but these male master-student relationships show up very differently in the two men's medical writings. In al-Azraq's text, Tashil al-Manafi' fi'l-tibb, as well as its reception in the following centuries, it is clear that he participated in a broader movement of ulama in Yemen. These texts of ṭibb, pitched at non-physician, literate men, instructed and encouraged their audiences to heal the broader Muslim community who were supposedly in serious need of their help. Through their compilations, abridgements and experimentation, al-Azraq and other ulama assembled beneficial and accessible texts for this purpose. Across the sea, Nagauri was urged by Sufi teachings to give up his lucrative administrative position at a court and, thus, had ended up a poor and pious physician. As he details in his Persian text, Shifa al-Maraẓ, Islam had motivated him to become a healer, yet he sought out both Muslim and non-Muslim teachers among yogis, hybridized the two formal medical systems he had learned, and treated both Muslim and "Hindu" patients with this hybrid medicine, all the while calling it ṭibb. Though these men were not anthologized within physicians' histories of the great men of medicine, I argue that masculinity shaped both their access and approach to ṭibb as well as their choice to write on the subject. Drawing on a growing body of work in the history of science and Islamic studies, this paper explores the construction of "scientific masculinities" across these Arabic and Persian medical texts.