This chapter introduces the goals and benefits that are motivating companies to report on their sustainability activities and provides an overview of the historical development of sustainability reporting over recent decades. The presentation of challenges in sustainability reporting is followed by a critical appraisal of approaches to overcome these problems. The authors suggest a double-path approach which combines the strategic inside-out approach of performance measurement and management with the outside-in approach of adopting to the external requirements and conclude with consequences for the field of sustainability communication.