Adopting and developing the new generation of information systems will be essential to remain competitive in a quality conscious health care environment. These systems enable physicians to document patient encounters and aggregate the information from the population they treat, while capturing detailed data on chronic medical conditions, medications, treatment plans, risk factors, severity of conditions, and health care resource utilization and management. Today, the knowledge-based information systems should offer instant, around-the-clock access for the provider, support simple order entry, facilitate data capture and retrieval, and provide eligibility verification, electronic authentication, prescription writing, security, and reporting that benchmarks outcomes management based upon clinical/financial decisions and treatment plans. It is an integral part of any information system to incorporate and integrate transactional (financial/administrative) information, as well as analytical (clinical/medical) data in a user-friendly, readily accessible, and secure form. This article explores the technical, financial, logistical, and behavioral obstacles on the way to the Promised Land.