Companies have invested large amounts of money on information systems development. Unfortunately, not all information systems developments are successful. Software project failure is frequent and lamentable. Surveys and statistical analysis results underscore the severity and scope of software project failure. Limited research relates software structure to information systems failures. Systematic study of failure provides insights into the causes of IS failure. More importantly, it contributes to better monitoring and control of projects and enhancing the likelihood of the success of management information systems. The underlining theories and literature that contribute to the construction of theoretical framework come from general systems theory, complexity theory, and failure studies. One hundred COBOL programs from a single company are used in the analysis. The program log clearly documents the date, time, and the reasons for changes to the programs. In this study the relationships among the variables of business requirements change, software complexity, program size and the error rate in each phase of software development life cycle are tested. Interpretations of the hypotheses testing are provided as well. The data shows that analysis error and design error occur more often than programming error. Measurement criteria need to be developed at each stage of the software development cycle, especially in the early stage. The quality and reliability of software can be improved continuously. The findings from this study suggest that it is imperative to develop an adaptive system that can cope with the changes to the business environment. Further, management needs to focus on processes that improve the quality of the system design stage.