Two cases of user-environment mismatch and tensions as well as ways and modes of the users’ adjustments to strictly pre-defined physical environments are presented and discussed in the article. The first case is historical – it analyses consequences of a mass housing program in the former Soviet Union where tens of millions of families coming from very different cultural and social backgrounds had to adjust their everyday life to extremely standardized physical settings. Using the results of the study carried out during 1978-1985 in several Soviet cities, the main areas of tensions and sources of discomfort reported by residents, are described and discussed. The second case focuses on a recent trend in workplace design called activity-based offices representing work environment where employees don’t have their own (fixed, personalized) workplaces but are supposed to move from one zone to another, depending on the task or activity they are involved in. A study of activity based offices carried out in Estonia in 2018, indicates that employee’s participation in the planning and designing of their work environment may help them better adjust to a novel and unusual workplace layout. The message from the both cases is that a better communication between planners and end-users as well as collaboration between them may help to reduce misunderstandings and the user’s dissatisfaction with the physical environment where people have to live and work.