Abstract
Debate over the proper approach to modern contract interpretation continues even in this era of modern contract interpretation where context is always considered. This paper identifies and contrasts two rival approaches to contract interpretation: “prescriptive contextualism” which demands that contract interpretation start with plain meaning, and only then go on to consider textual context, extra-textual context and finally commercial sense; and “holistic contextualism” which involves consideration of those same factors but is not fussy about the order. In setting out the two approaches, I provide an exposition of the present law of contract interpretation. Then, I consider the main arguments that can be advanced by proponents of the two approaches, and conclude by offering my own arguments that, I suggest, tip the scales in favour of holistic contextualism: the prescriptive process inhibits identification of viable interpretation, and is overly dependant on which words are used to start the interpretive process.