Most studies on Islamic law focus on the openness of the door of ijtihad and the availability of various reasoning tools as evidence for the flexibility of Islamic law. Examples of flexible interpretations and rulings of Islamic law, dispersed across time and geographic areas, are often provided as evidence of Islamic law adaptability. It is assumed that qadis and muftis flexibly and pragmatically utilized tools of interpretation simply because of their availability and permissibility. I argue that while the availability of tools of interpretation is necessary for Islamic law to adapt, they are not sufficient. Islamic legal change is an individual endeavor that hinges on muftis and qadis. Muftis and qadis lived within specific socio-economic and political contexts that shaped their willingness to utilize tools of ijtihad. They also operated within the boundaries of a profession and were, consequently, affected by incentives that emerged out of the structure of their professional institutions. To understand the dynamics of change in Islamic law and jurisdiction, we need to understand the motives of the agents operating the system. It is the balance sheet of incentives and motives of qadis and muftis that controlled the frequency and scale of change in Islamic law. In this paper I focus on the institutional constraints muftis and qadis faced in interpreting Islamic law in Ottoman Syria. I reconstruct the Islamic legal system in which they operated to analyze their motives to flexibly interpret and apply Islamic law. I show that the individualistic structure of Islamic judicial institutions, their lack of central organization, and the legitimization process qadis and muftis faced constrained the frequency by which they resorted to ijtihad tools. I utilize classical works on adab al-qadi and adab al-mufti to frame both professions' legitimacy criteria. I base my analysis on fatwa collections of Khayr el-Din al-Ramli, known for his flexible opinions. Secondary works on Islamic courts in Ottoman Syria and qadis' decisions are consulted. I find that while innovation was not necessarily prohibited, it was not encouraged. The legal system provided incentives to conform to what existed, rather than innovate. Innovative attempts were left individualistic and uncoordinated. The cumulative consequence limited the scale of innovative rulings, confined change to local and individual incidences, and prevented their spread.