Strengthening the rule of law and promoting access to justice in developing countries have been longstanding international policy objectives. However, the standard policy tools, such as technical assistance and material aid, are routinely criticized for failing to achieve their objectives. The rare exception is paralegal aid, which is almost universally lauded by policymakers and scholars as effective in promoting the rule of law and access to justice. This belief, however, rests on a very limited empirical foundation regarding what paralegal programs accomplish and under what theory they operate. This paper critically examines the conventional wisdom surrounding paralegal initiatives through case studies of two successful paralegal programs in post-conflict Timor-Leste that are broadly representative of the type of initiatives commonly implemented in developing countries. These programs did improve access to justice services, bolster choice between dispute resolution forums, and increase local knowledge of progressive norms on human rights and women's rights. Yet, as this article shows, even successful programs can expect to achieve only incremental gains in promoting the rule of law because advances largely depend on alignment with the priorities of powerful state and non-state actors, donors, program implementers, and paralegals themselves. To date, the literature has not acknowledged these limitations. This article addresses this gap by demonstrating that paralegal aid faces multiple challenges that mean paralegals cannot necessarily transcend or modify deep seated norms and power structures. These issues include principal agent-problems due to the extensive delegation required, internal limitations resulting from paralegals' limited authority and independence, and external constraints from state and non-state justice actors. Paralegal programs also face program design, implementation, and sustainability challenges. Consequently, scholars, practitioners, and policymakers need to adopt a more balanced view of paralegal aid.