Various factors can impact someone’s efficient and effective use of technology. However, thesetopics are often disconnected and, as a result, may only partially describe the ecosystem of factors that can influence an individual’s experiences with technology. Case studies investigated the intersection of mandatory technology usage and discretionary AT, accessibility, and ease of use features to better understand the factors that can impact user’s effective and efficient use of computer personalization. Barriers, facilitators, and perpetuating factors were identified. The further re-examination of case study data through various lenses led to three new, proposed contributions related to the personalization of user experiences. 1) The Gulf of Attribution theory may potentially describe the vulnerabilities people may encounter when making causal attributions, which can impact their interpretation and understanding of systems. 2) The Integration of Technology Personalization into Existing Practice (ITPEP) model may potentially describe the lifecycle of personalization technology adoption, acceptance, and integration into existing usage. The ITPEP model also suggests how the successful or unsuccessful integration of personalization changes may also impact people’s future attempts to optimize their user experiences. People, who adopted, accepted, and integrated their personalization changes, appeared to experience an increase in self-efficacy and reported an increased desire in making more personalization changes. Conversely, people who rejected such changes, appeared less willing to explore personalization’s potential to improve their user experiences. Case study findings were combined with a multidisciplinary critical review of theories, models, and frameworks to identify additional factors that can influence people’s digital experiences and meaning processes. This led to the development of 3) a novel, conceptual framework for Digital Rapport. The proposed Digital Rapport conceptual may potentially describe the level of meaning alignment between the individual, the system, and their circumstances. The thesis concludes that personalization technologies should consider expanding to also include meaning-alignment in addition to ability alignment to better support people’s intuitive and meaningful interactions with technology.