Smallholder tree plantation, now on the increase in Indonesia, has long been practiced by rural farmers as a strategy to optimize the expected utility of land, labor and other constraints. Increasing demand for timber has driven a shift toward commercialization of smallholder forestry. However, smallholders face huge challenges when they seek for commercial markets in the form of complex regulatory frameworks applied to smallholder plantations. This paper discusses the case of smallholder plantations in Gunungkidul District (Indonesia), considered one of the most commercialized timber marketing hubs for local, national and international markets. It analyzes how opportunities and challenges, resulted from different regulatory frameworks, affect the competitiveness of smallholder forestry practices. In this paper, regulatory frameworks are defined as not only regulations issued by public administrators at the domestic (local and national) level, but also cover the emerging market-based regulatory frameworks, i.e. voluntary certification of sustainable forestry and mandatory timber legality verification.