Despite high expectations for the value of e-business in healthcare, its adoption remains poorly understood and under-researched. The adoption and effective utilization of e-business in the healthcare industry can potentially lead to many benefits, such as: an increased accessibility to healthcare providers, improved work-flow efficiency, a higher quality of healthcare services, decreased scheduling conflicts, and reduction in healthcare costs. Healthcare organizations have started to fully make use of e-business technologies to overcome many of the challenges they face. However, healthcare executives have found it increasingly difficult to justify rising IT expenditures and are often under pressure to find a way to evaluate the contribution of their e-business investments to business performance, as well as to find reliable ways to ensure that the business benefits from the investments are actually realized. Hence, the case study approach was conducted to examine the evaluation practices and processes of their e-business investment. The key objectives of the study are to: (1) examine current e-business investment evaluation and benefits realization practices and processes among different types of healthcare organizations; and (2) identify issues and factors that are critical in evaluating and managing e-business investments in healthcare organizations. One contribution of the study is the examination of the relationship between e-business investments and evaluation practices and processes of healthcare organizations.