Ibn Kemāl Pashazade (d. 1534) was a poet, historian and Islamic jurist. From year 1525 until his death, he held the highest position of the Islamic religious learning: the position of Shaykh al-Islām. In his famous treatise, Risāla al-munīra, he addresses imams of the mosques in various provinces of the burgeoning Ottoman Empire. In this epistle, he calls on these scholars to teach and guide the Muslim community in the face of confusion and disarray within the society of his time. This call to the ‘ulemā’ to teach proper ways of Islam is ultimately linked to an important theme within his writings, in particular to the issue of certainty and doubt. In this paper presentation, I speak about Ibn Kemāl’s works through a lens that looks at his approach to the question of knowledge. I explore places within his arguments that call into question the singularity of only one understanding of the Revelation. In addition to this, the paper further explores how by advocating the importance of the Sharī‘ā, Ibn Kemāl espouses Ibn Taymiyya’s insistence of the Islamic law and a way of life that was inherited from the Prophet. Conversely, Ibn Kemāl’s reiteration that true knowledge is only esoteric knowledge, which is, in particular, reminiscent of Ibn ‘Arabā’s teachings, places him in the camp of thinker who consider that knowledge of the divine and the right path does not simply come from the established sources. By focusing on the latter issue, Ibn Kemāl continues the legacy of earlier Islamic scholars who questioned the foundations of and approaches in establishing knowledge. By engaging in the debate of whether revelation or other sources of knowing, in his case esoteric mystical experience, results in true knowledge, Ibn Kemāl throws doubt over the epistemological foundation of Islamic religious learning. Yet, his insistence on certainty and orthodoxy of the Sunna, he seems to have deep trust that such confusion is not permanent and that one can escape from it with the right guidance to a place of certainty and social stability. In other words, Ibn Kemāl did not seek to create ambiguities, but rather pointed to the problematic spiritual and religious issues that were discussed in his days. Thus, throughout his risāla, it is clear that Ibn Kemāl hopes to come up with the solution in order to end confusion and instill certainty.