Digitization has fundamentally changed businesses, segments of society, and individuals’ life. There are two changing perspectives in the history of digital transformation. One is the expanding boundary of digitization, from a transformation within organizations, through innovations in interactions among businesses and customers, to societal changes at large. The other is the shifting focus of digitization, from digitizing production and delivery of goods and services, to digitizing all aspects of everyday life. However, extant research in digitization has not paid much attention to its impacts beyond the organizational boundary and the business relationships, and often adopted a technology-deterministic view of digitization. In this dissertation, I propose the notion, “digital citizenship”, to reexamine the nature and impact of digitization from a human-centric perspective and embed digitization in a broader social context. To elaborate on the notion of digital citizenship, I study the informative, automate, and transformative roles of digitization, and why and how various types of digitization enhance overall welfare for all parties of digital citizens. These three studies, presented as separate essays herein, i) evaluate the effectiveness of Intelligent Transportation Systems adopted by local governments transforming urban traffic management, ii) explore enhancing drivers’ traffic safety effort due to the deterrent potential of automated surveillance technology on the road, and iii) examine the mechanisms of information provision on customers decision making on churn and the implications for firms on the challenge of digital channel attribution. In regard to each, I discuss the relevant theory, the methodology, data sources, results, and implications. I conclude by highlighting the contributions of my work, and possible avenues for future research.