The papers presented in this open access book address diverse challenges in decarbonizing energy systems, ranging from operational to investment planning problems, from market economics to technical and environmental considerations, from distribution grids to transmission grids, and from theoretical considerations to data provision concerns and applied case studies. While most papers have a clear methodological focus, they address policy-relevant questions at the same time. The target audience therefore includes academics and experts in industry as well as policy makers, who are interested in state-of-the-art quantitative modelling of policy relevant problems in energy systems.  The 2nd International Symposium on Energy System Optimization (ISESO 2018) was held at the Karlsruhe Institute of Technology (KIT) under the symposium theme "Bridging the Gap Between Mathematical Modelling and Policy Support" on October 10th and 11th 2018. ISESO 2018 was organized by the KIT,the Heidelberg Institute for Theoretical Studies (HITS), the Heidelberg University, the German Aerospace Center and the University of Stuttgart.