The healthcare environment is becoming increasingly dependent on health information technology, with providers, patients, payers, and other players producing and sharing information to improve healthcare delivery. This, in turn, has brought the issue of Health Information Infrastructure (HII) to the forefront of policy, design, and law. While several studies have examined each element of HII, little attention has been paid to the infrastructure in its totality as a collection of technologies, institutions, standards, and practices. Healthcare practitioners and researchers typically follow governmental guidelines (or federal policies) related to technology, standards, institutions, and legal frameworks, resulting in a lack of practical perspective. In order to fill the gap, this dissertation focuses on medication reconciliation as an example of the bigger phenomenon of HII. In particular, the dissertation examines a community-level medication reconciliation process to understand the key challenges facing the development of HII, how the challenges feed into each other, and how they can be met as a whole. Following a mixed methodology, involving workflow study, focus group discussions, and in-depth interviews, the dissertation examines "data friction" along technical, institutional, regulatory, and legal dimensions. The study, as such, contributes to a better understanding of the HII and the practical challenges that hinder the seamless flow of information in the healthcare environment. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]