Increasing dependency on digital technologies introduces queries related to well-being–when and how digital technology poses a threat, or when it is the most appreciated by users? People have some expectations before using technology, which sometimes may be met, but there might be a mismatch at other times. Nevertheless, the digitalization of services advances and companies modify existing or produce new technologies that do not satisfy users' demands, putting their well-being at risk. Through an empirical inquiry, the present research explores experiences with technologies to shed more light on the main factors that enrich or diminish technology value and influence well-being. Exploiting the circumstances created by the COVID-19 pandemic that fast-forwarded technology use and development, an online inquiry was conducted to assess positive and negative experiences of technologies, focusing on the contexts of work, learning, entertainment, information-seeking, and health. The findings from 578 participants indicate that depending on the role of technologybeing a substitute for certain activities or an opportunity to perform them differently–consequences on well-being can more or less follow expectations. The results are discussed in the context of past research and practical implications for, e.g. technology design or managerial changes that could help overcome users' current challenges.