The flexibility of information systems to business change is examined. Four organizations were used as case studies, where information systems development and usage was investigated using interpretivist research methods. The case data reveals that information systems development using systems development methodologies which are bounded in business projects is largely an inflexible process that is not adequately catering for changes in business requirements. The alternative of tailorable information systems is proposed and the case is made for the spiral of change model of tailorable information systems as a more flexible development process.