The importance of studying challenges in implementing information technology solutions in health care organizations is highlighted by the huge investments in health care information technology (HIT) which has been spurred by recent government mandates. Information technology can help improve health care delivery cost by facilitating the standardization of work processes or routines and reducing variations among them. Set in a premier 950+ bed hospital in the south eastern part of US, this dissertation consists of two studies examining the challenges involved in implementing HIT solutions. In the first study, we seek to gain deep insights into how the process of creating a patient’s chart evolves over time in a health care institution. The second study focuses on the users of Electronic Health Records (EHR) system, investigating the compliance behavior of various providers with respect to patient records in the system. In the first study, through the lens of Activity theory our results show that the charting routine is implicated by the following environmental factors: (1) Tools, (2) Rules, (3) Community, and (4) Roles, and by individual factors: (5) Computer Self-Efficacy and (6) Risk Propensity. In the second study, our results indicate that there is a substantial effect of subculture of the different occupational groups on IT security compliance intent and behavior in a health care institution.