The correlation between the quality of information systems (IS) development practices, the products they shape, and systems maintainability has been well established. Several organizations have expended large amounts of money on ineffective software that have attracted high maintenance activities, which consume a disproportionate share of IS development resources. The IS quandary is how to reverse this trend, and free up resources for more productive organizational endeavors. This chapter presents a review of a variety of IS quality-oriented approaches (based on research findings and dispassionate practitioner accounts) and an indication of their advantages and weaknesses, and the development environments and contexts for which they are most suited. These techniques are available to software developers to be used individually or in synergistic combinations to confront the prevalent problem of poor software quality and reduce its unfavorable impact on software maintenance.