The increasing demand for food and fiber, the need for climate change mitigation and adaptation as well as for environmental protection impose severe challenges on land systems worldwide. Solutions to support the transformation towards a sustainable development of land systems are needed. One response to the multiple challenges is the introduction of policy options aimed at steering land use activities towards a bundle of societal goals. However, it is difficult to empirically foresee the effectiveness and unintended consequences of policy options prior to their deployment. A second response is environmental education because human consumption behavior, among other factors, strongly influences natural ecosystems. However, it is a non-trivial task to develop effective communication strategies for complex topics such as sustainable land management. In both cases, modeling can help to overcome the different obstacles along the way. In this thesis, dynamic process-based social-ecological models at the individual scale are developed and analyzed to study effectiveness and unintended side effects of policy options, which promote agricultural management strategies and were intentionally designed to cope with multiple societal challenges. Two case studies of political intervention are investigated: the promotion of perennial woody crops in European agricultural landscapes for a sustainable bioeconomy and governmental supplementary feeding programs to cope with climate risks in pastoral systems in drylands. These two case studies are complemented by the development of a serious online game on sustainable land management in general that bridges the gap between land use modeling and environmental education. Simulation results of this thesis provide insights into (i) the performance of the politically promoted agricultural management strategies in meeting various intended goals such as poverty alleviation or the maintenance of biodiversity and ecosystem services, (ii) the emergence of unintended (environmental and social) side effects such as land use conflicts, land degradation or cost explosion and (iii) the mitigation of such side effects by appropriately adjusting the design of the policy options. These insights are enabled by representing temporal as well as spatial variability in the developed models. Furthermore, different mechanistic approaches of transferability analyses based on stylized landscapes are developed and applied. They enable to check whether and in what respect policy impacts actually differ substantially between regional contexts, to identify what regional factors steer the impact and to derive indicators for grouping regions of similar policy impacts. Finally, based on a conducted survey-based evaluation and experiences from various applications, the value of the developed serious game for environmental education is revealed and discussed.Altogether, this thesis contributes to model-based decision support for steering transformation towards the sustainable development of land systems in an appropriate way. This is done by developing appropriate social-ecological modeling approaches, by performing specific policy impact analyses in two transformative agricultural systems using these models and by providing a model-based communication tool for environmental education.