Much attention has been directed to the creation of new institutions and processes in postconflict Timor-Leste; less emphasis has yet been placed on the individuals who operate and navigate this still incomplete system. Justice sector institutions function with practical constraints of budget and logistics, but are also subject to indirect pressures from the political sphere. Legal professionals face an unenviable situation in various respects—due to linguistic and, increasingly, regulatory hurdles, many are unable to enter courtroom practice. Those who do find work in a tribunal setting are often faced with daunting casework backlogs and unclear responsibilities, which may produce insular and defensive professional cultures. Outside the courts, jurists are leveraging influence as political operators, and informally as conduits of state-oriented information to their communities. This article, comprising research toward the author's doctorate, considers the interplay of process and personality in the Timorese justice sector and discusses implications for development.