This chapter examines the issues surrounding the development of adaptive evolutionary systems by evaluating the characteristics of contemporary development paradigms. It categorises these characteristics as advantages or limitations with respect to the purpose of servicing adaptive evolutionary systems’ requirements. The chapter considers the evolution of development paradigms and concludes that a key limitation in each case has been the preoccupation with addressing the shortcomings of the previous paradigm’s implementation. The maturity of the paradigm is seen as a significant element in determining what the current research issues for that paradigm will be and this observation is used to recommend the line of development that should be taken to avoid recurrent pitfalls. The issues extracted are structured into a framework for the evaluation of any given approach with respect to its suitability for the development of adaptive evolutionary systems. Recommendations are given for future work including recommendations outside the accepted sphere of information systems research.