Tobacco production in Zimbabwe has increased sharply in the recent two decades mainly from smallholder farmers in communal areas and those who were the beneficiaries of land redistribution including the fast-track land reform programme in the country since the beginning of the new millennium. This chapter analyses and explains the state of the smallholder tobacco sector which faces the twin challenges of the ‘rock’ of unpredictable market conditions and the ‘hard place’ culminating from environmental degradation that is inherently linked to the sector. It adopts the theoretical framework of sustainability as a lens to view these challenges. By using an institutional approach, the study relies on secondary data covering policy issues, events and descriptive statistics of the smallholder tobacco sector in Zimbabwe. Uncertain market forces characterised by an inconsistent agricultural policy, pricing model and payment system compromise earnings of smallholder tobacco producers. Smallholder tobacco production is now a significant contributor to deforestation, mainly of Miombo woodlands, which puts the sector's productivity at stake and thus undermines its long-term sustainability as forest resources are getting depleted. The smallholder tobacco farming sector consists of a turbulent trajectory that requires more work on institutions to ensure sustainability.