Contracts and the law seek to remove uncertainty and provide predictability. Contracting parties need clarity as to their performance, roles, rights and duties. For lawyers, predictability is also about predicting how a contract, intertwined with the applicable law, will be interpreted and applied if a legal dispute arises. The increasing use of images in contracts can enhance the parties’ shared understanding and remove the need for legal interpretation. But when the need arises, images raise new questions: for centuries, contracts’ legal interpretation has been about the text – now there is a need to interpret images embedded in contracts, either alone or in combination with text. This chapter explores the needs and expectations of contracts’ different audiences and how they could be better aligned at the contract design stage, so as to guide and shape business and legal users’ image interpretation, provide predictability and prevent unnecessary disputes.