The ‘riches versus poverty’ debates in the Islamic tradition have been attested in the sources from the late 8th – early 9th centuries CE. Centered on the merits of poverty (al-faqr) and wealth (al-ghinā) and the question of precedence of one condition over the other with regard to spiritual rewards, they display a spectrum of views on the relationship between wealth, poverty, and religious merit among medieval Muslim scholars. On one end of it was the position that exalted poverty and emphasized the vanity of worldly possessions and the dangers associated with the accumulation of wealth. At the opposite end was the view that endorsed wealth, considering it either as a reward or a gift from God, while highlighting the disadvantages of poverty. While these debates range across the boundaries of various Islamic intellectual traditions and literary genres, this paper focuses on the ‘riches versus poverty’ debate within the Sufi tradition, as discussed in classical Sufi manuals from the 10th to the 12th centuries CE. The close association of poverty with piety and the exaltation of poverty as a condition inducive to acquiring spiritual rewards has been characteristic of the Sufi tradition, with poverty (faqr) being traditionally included among the stations (maqāmāt) on the Sufi path. However, some Sufi figures, such as Aḥmad Ibn ‘Aṭā’ (d. 309/922), reportedly argued for the precedence (faḍl) of wealth over poverty, thereby challenging the status of poverty as religious ideal. This paper examines how the authors of the classical Sufi manuals presented this intra-Sufi debate against the background of the consolidation of the Sufi tradition and the need to reconcile a religious ideal of poverty with historical reality. In particular, the paper highlights the shift towards the ‘spiritualization’ of poverty (equating poverty to spiritual detachment rather than lack of material possessions) and the restriction of its relevance as a virtue to specific groups/contexts, both these tendencies manifest in the account of the debate in al-Ghazālī’s (d. 505/1111) Revival of the Religious Sciences (Iḥyā’ ‘ulūm al-dīn), the latest among the analyzed sources. Through this case study of riches and poverty, the paper will shed light on the processes of negotiation of religious virtues and moral orientations within the Sufi tradition and the medieval Muslim societies.