It is well known that after the Arab conquests of Egypt in the 640s, the gradually expanding Islamic state heavily relied on Greek and Coptic-speaking administrators. Not only had duxes, pagarchs, and bishops overseen taxation, imperial communication, and the provision of food supplies for centuries, but they also inhabited positions equipped with remarkable discretionary powers. While the executive roles of these bureaucrats in the burgeoning Islamic state administration are now relatively well understood, the judicial functions they had as mediators, arbiters, and, at times, judges have elicited few scholarly inquiries. By focusing on how ordinary Egyptians sought legal recourse by petitioning and bringing their cases before these lower levels of jurisdiction, we can refine our understanding of the workings of the Islamic state machinery and, more importantly, complicate existing accounts about the emergence of Islamic justice. Using Arabic, Greek, and Coptic documents, this paper rationalizes the individual calculations ordinary Muslims and Christians in seventh/eighth-century Egypt made when deciding where to seek legal recourse. What propelled al-ʿAllana, a Muslim woman from the Fayyum, to initiate divorce proceedings against her husband with the local ḥakam (P.Michael. A 1346) rather than responding to his request to resolve the issue through conciliation? Why did John the Deacon bring his lawsuit against Philemon for the estate of a deceased family member before arbiters (P.Col. 600) rather than a formal court? Why did the monks of a monastery in Upper Egypt, after one of their brothers illicitly brought a stranger into his cell, decide not to expel him and have him draft a formal legal document declaring that he would submit to the laws of his monastery (P.BL. Or. 9536)? By reading the documentary evidence through a social history lens, this paper argues that “confession” and “communal belonging” constitute insufficient categories to understand how ordinary people navigated the complex legal infrastructure of post-conquest Egypt. Instead, I argue that the papyri present a much different picture: the anticipated legal outcome, finality of judgment, legal procedure, personal wealth, and status were often much more critical factors when picking legal forums. Because Islamic legal studies have paid little attention to documentary evidence, let alone from lower, non-Muslim levels of jurisdiction, this paper offers a fresh perspective on the earliest period of Islamic justice and hopes to contribute to a growing body of literature that accounts for the development of Islamic law as a multilateral and multi-confessional project.