The long-distance trade that connected the prized medieval markets of the Indian Ocean with those of the Mediterranean has been the subject of great scholarly interest. In spite of the absence of developed near eastern institutions of trade (i.e., banks, guilds, maritime navies) such trade was regularized and efficiently responded to changes in international markets. How was this possible? The Genizah business letters of the Jewish community of Cairo, during the tenth through twelfth centuries, illustrate how medieval trade in the Near East was performed through a reciprocal system of 'formal friendship' ties between traders. S.D. Goitein argued that the formation of long chains of personal ties allowed for the long-distance exchange of people, goods, and most importantly, market information. The key feature of such relationships was a merchant's network of ashab, through which he could engage in trading outside his immediate city or region. This concept of suhba as the driving force behind the social organization of early medieval trade in the Near East continues to dominate. While the Genizah letters provide compelling evidence for the above use of suhba in facilitating early medieval trade, these sources do not explain how suhba and other practices unfolded in subsequent centuries, and whether it was different among Muslim or Christian traders. Whereas the early sixteenth century is recognized as a major realignment in Indian Ocean trade, brought about by European mercantilism, the period between the thirteenth and sixteenth centuries has not been sufficiently examined for changes in business practices. My paper aims to address this lacuna by analyzing the use of the term suhba in its various forms (e.g., sahib, ashab, ashabbuna) as it appears in Arabic business letters, diaries and legal responsa from the thirteenth to sixteenth centuries. I will employ selections from the edited Quseir Qadim and Vienna collections of Arabic business letters to provisionally argue that the later use of suhba by Muslim traders reveals more ambivalence regarding “formal friendship”, if indeed it existed among these traders and brings into question the role of official intermediaries and formalism in trade.