Between the years 1372 and 1374, Ibn Khaldun (d. 1406) was living a life of high status, teaching and and pursuing knowledge in Fez. He set about writing his treatise, Shifa’ al-sa'il fi tahdhib al-masa'il, in response to a debate current at that time. The great Granadan jurist of the Maliki school, Abu Ishaq al-Shatibi (d. 1388) had been asked to weigh in on the proper approach of the adept along the Sufi Path. Was it necessary to have the guidance of a Sufi master, or could one take advantage of the large body of literature in circulation on the subject, and content oneself with the written wisdom of the fields’ luminaries? In a letter to the scholars of Fez, al-Shatibi had detailed the ongoing disputes on the matter, and asked his peers for their opinions. Whether invited or not, Ibn Khaldun undertook to enter the fray and to write a treatment of the issue, bringing to bear his expansive knowledge, not only of Islamic law but also of Sufism itself. Ibn Khaldun was in a unique position to do this. As a tribal negotiator, he had worked tirelessly to build bridges between disparate communities. He would therefore have been keenly aware of the hold of the Sufis over the Moroccan countryside and the practical realities of Sufism’s role in peoples’ lives. In the Muqaddima, Ibn Khaldun refers to Sufism as one of the Islamic religious sciences—after speculative theology (‘ilm al-kalam) and before dream interpretation (‘ilm al-ru’ya). This paper will address how the Shifa’ fits into the corpus of Ibn Khaldun’s work as well as how the contents shed light on Sufism in the 14th century Maghreb.