This article traces the history of the medieval oasis city of Sijilmassa, southeastern Morocco, and that of its modern, continuation city of metropolitan Rissani in the Tafilalt region. Elements of mobility and transition are discussed in light of the prominent historical role of the urban settlement in Tafilalt in long-distance trans-Saharan trade infrastructure. These elements are developed with a focus on the region’s Jewish communities, their socio-spatial characteristics, the employed toponymy with respect to Sijilmassa, and the material culture. Within the material culture of Tafilalt’s Jewry until the 1950s and 1960s (that is, upon their dramatic emigration from Morocco, mostly to Israel), the article analyzes in an original manner their traditional marriage contracts (ketubah-s) as a textual and especially as an esthetic artifact. The analysis interprets the visual imagery that appears in these manuscripts—an imagery that corresponds with global Jewish symbols, with the vernacular architecture in the Tafilalt, and with wider regional, trans-Saharan conceptual motifs. Revealing the composite symbolic imagery and decoding the visual repertoire of the ketubah-s against the rich cultural histories of the pre-Sahara region—with affinity to both northern Morocco and sub-Saharan, “black”, Africa—necessitates an interdisciplinary approach. This study brings together area studies (of the Middle East and Africa), art histories (of architecture and built forms, artifacts, and manuscripts), cultural studies (critical intra-group relations between Arabs, Berbers and Jews), and human geography (forms of settlements and long-distance trade activity)—in a type of meeting that is quite uncommon in the relevant research literature. Its contribution lies in tracing the dissemination of ideas and material cultures among less researched groups (southeastern Jewry) and regions (pre-Saharan) in Morocco, through engaging a transdisciplinary lens that requires an intimate acquaintance with associated research historiographies.