Digital libraries are an important information source of high quality information for various user groups in education, research and industry. With an exponential growing amount of digital content, digital libraries face the challenge of enhancing the support for information seeking. This paper takes the users’ perspective and investigates whether the users of digital libraries perceive that their information demand is satisfied. The approach taken is an empirical qualitative study with various user groups in two different countries. From an information demand perspective, the main result is the support for the conjecture that there is a coupling between the user’s context and the information demand: The analysis of the data collected in the interviews and of the observations shows a connection between the respondent’s role (teacher, researcher, student, etc.) and the activities for which the searched information is needed (assignment, lectures, scientific work, etc.). The observation from Jönköping that researchers seem to be more aware of their information demand was not confirmed in the Karelian part. Furthermore, a usability questionnaire was used to identify shortcomings and propose improvements in the digital library systems applied at the two study locations.