This article examines whether a three-year learning-based work community intervention resulted in changes in working community-related interaction factors and occupational well-being among Finnish and Estonian school staff. It reports the types of changes in working community-related interaction factors and their associations to the subjective occupational well-being and general occupational well-being of the working community. The initial quantitative survey data were collected in Finland (n = 486) and Estonia (n = 1330) in 2010 using the "Well-being at your work index questionnaire." The same measurement tool was used in 2013 to collect final survey data from school staff members in Finland (n = 545) and Estonia (n = 974). The data were analyzed statistically with percent, mean, SD, Mann-Whitney test, sum variables, one-way analysis of variance and Spearman's correlation. Changes were detected in factors related to working community interaction; in particular, statistically significant changes in work management and time use were detected in Finnish schools. Working atmosphere and appreciation of others' work, cooperation and information, and work management and time use were associated to both the subjective occupational well-being and general occupational well-being of the working community. Schools should plan and implement development activities to promote the subjective occupational well-being and general working community occupational well-being. Development work should focus on working community-related interaction, such as trust between workers. Principals should draw particular attention to principal-subordinate relationships and to providing information about changes.