This chapter presents a summary of some features of soft systems methodology-SSM, and of critical systems thinking-CST as they have been experienced from the point of view of the field of applications of information technology. It highlights the manner in which CST completes SSM in the context of the design of computer support in the form of HYPERSYSTEMS, and evidences some problematic aspects of the two approaches which push the practitioner into philosophical issues. One concluding hypothesis is that further developments of systems practice must be sought at the interface between formal science, political ethics, analytic psychology, and religious thought. For tutorial purposes, a great amount of literature is related to these issues.