This chapter examines from systems and livelihood perspectives, with Nemoral and Boreal forest zones of the Global North and Sweden as examples, how forestry may meet current and future sustainability challenges both as a traditional resource base and with respect to other ecosystem services. Previous and current forest policy/governance is briefly described against the background that Swedish forestry is based both on huge holdings by few industrial owners as well as on a multitude of small individual, often family owned, forest estates. Successful delivery against environmental objectives will require careful balancing of interests and the active participation of local forest owners. Cumulative effects of old and new societal demands on forestry and their impact on local livelihoods poses in this respect a systemic risk as economic and social sustainability often gets limited consideration. There is a need for a more synoptic and systemic analysis of how forestry is affected by multiple, partly contradictory, demands from an increasing array of stakeholders, in order to enable a move towards a biobased economy. Stakeholder-based group modelling is a potentially powerful analytic and conflict reducing approach that could help improve forestry’s contribution to the acute need to handle the climate change and current sustainability challenges.