The design and implementation of healthcare information systems (HIS) is problematic as many HIS projects do not achieve the desired outcomes. There exist a number of theories to enhance our ability to successfully develop HIS. Examples of such theories include ‘fit’ and the sociotechnical approach. However, there are few empirical studies that illustrate how to understand and operationalize such theories at the empirical level needed for HIS design. This chapter introduces a practice support framework that bridges the gap between the theoretical and empirical aspects of HIS design by identifying specific process and information practice supports that need to be considered to actively produce fit of an HIS within a healthcare setting. The chapter also provides an empirical case study of how practice support was used to develop a computer based tool in the domain area of palliative care severe pain management.