While drafting a contract, the drafter takes into account the specific requirements of the involved parties. Depending on the complexity of the contract, this means that the contract drafters often self-prescribe the rules that the contract is governed under. However, are these rules valid? What statutory rules and regulations affect such liberty of the contract drafter? Do courts – both domestic and international – pay heed to such rules, or disregard them in favour of general principles - both legal and otherwise, such as the significance of the natural meaning of the contract’s language, upholding the general common-sense based practices in similar transactions, upholding public interest? This paper looks at the extent of liberty the drafters of a contract have and other choices that are available to the contract drafters when it comes to designing a tailor-made contract to fit the circumstances.