The Scottish Government has clearly stated its intention to increase woodland cover from 18% towards 25% of land area by 2050. This will rely heavily on publicly funded grant schemes to encourage woodland creation on private land. However, at present required rates of woodland expansion are not being met. Moreover, the benefits of new woodland are not guaranteed and depend on woodland type, spatial characteristics and cultural context. This paper reviews the rationale behind the current desire for expansion in Scotland and the barriers to its realisation. It argues that clearer articulation of woodland benefits is required, recognising both their variability over space and potentially detrimental impacts on other land uses. It further emphasises the role of landowner motivations and attitudes, and investigates the various influences on the decision-making process. Finally, it examines attempts to evaluate woodland expansion, particularly the use of indicators and spatial analysis, and the limitations of these approaches. It concludes by identifying areas for further research, emphasising benefit distribution, changing perceptions, and greater outcome evaluation.