While providing a few insights from my forthcoming critical monograph, this paper investigates the interplay between literary creativity and craftsmanship within the Arabic pre-modern urbanized context (9th-10th c.) as an exemplary case study of osmosis between cultural and creative spaces. Engaging with the current discourse on cultural heritage, the global frame of my research aims to provide background knowledge to the timely reflection on the creative processes and the resulting built-environment as inter-reliant entities ensuring the role of culture in social cohesion and its relation to creative and artistic freedom and diversity. The paper argues how historical moments of urban development linked to cultural enlightenment could have inspired some authors to develop a craftsmanship-inspired approach to literary writing as the rhetorical study of 9-10th-centuries treatises shows. The intervention is centered on interwoven, broad considerations on two main issues of research, namely, the reconceptualization of the binary categories of maṭbūʿ and maṣnūʿ (visceral/artificial) and the global socio-political Abbasid context of the belles-lettres-craftsmanship’s encounter. A few examples will be provided. The paper argues how the interplay between talent, literary craft, and ability enabled the Abbasid authors not only to explore, analyze, and employ their own languages and literary traditions as powerful tools, but also to reflect on new literary styles, models and perspectives whilst harmonizing a secular, progress-driven mentality.