This dissertation provides a context-specific theory to understand how city cultural organizations can best use digital stories and impression management to create a desired image or enhance public perceptions. The generated model describes how a digital storytelling information system can affect user impressions of a city and the outcomes of using such a system. The study responds to a growing interest among cultural organizations regarding how to use emerging information technologies in the communication of cultural content. An interpretive case study was conducted on the “Love Your City, Share Your Stories” digital storytelling initiative in Hamilton, Canada. Data collection included 95 one-on-one interviews with the general public, the gathering of documents, and the researcher’s personal observations of participants during the data collection process. A systematic approach of data analysis was utilized to capture participant opinions and visualize this information in a data structure. Theories from the literature on information systems, organizational impression management, and narrative transportation ground the study. Findings suggest that a digital storytelling information system can be a viable tool to share city cultural heritage information and positively affect people’s perceptions of a city. The overall outcome of creating/maintaining a positive favorable impression is shaped through a layered experience of benefits by the users. Users are first personally engaged and informed about a city’s cultural heritage (primary benefits), and then they are influenced and inspired positively towards the city (secondary benefits). Findings show that technology characteristics (i.e., media quality and story quality) are critical factors affecting outcomes of use, and that user characteristics and context of use both moderate this relationship. This research provides theoretical insights and practical recommendations for researchers and city cultural organizations wishing to explore the utilization of newer information technologies, such as digital storytelling, for impression management. / Thesis / Doctor of Philosophy (PhD) / This dissertation aims to understand how city cultural organizations can best use digital stories and impression management to enhance public perceptions. The generated model describes how a digital storytelling information system can affect user impressions of a city. The study responds to a growing interest among cultural organizations regarding how to use emerging information technologies in the communication of cultural content. Findings suggest that a digital storytelling information system can be a viable tool to share city cultural heritage information and positively affect people’s perceptions of a city. Findings show that technology characteristics (i.e., media quality and story quality) are critical factors affecting outcomes of use and that user characteristics and context of use both moderate this relationship. Theoretical insights and practical recommendations are provided for researchers and city cultural organizations wishing to explore the utilization of newer information technologies, such as digital storytelling, for impression management.