This study sought to understand generational and role differences in web usage of teachers, teacher candidates and K–12 students in a state in the USA (n = 2261). The researchers employed unique methods, which included using a custom‐built persistent web browser to track user behaviours free of self‐report, self‐selection and perception bias. Results revealed that all three groups utilized a variety of resources daily, but with some noticeable differences. For instance, (1) teachers and teacher candidates used the Internet on school devices much more than students; (2) they accessed general, multimedia, search, entertainment, shopping and social resources at a higher rate than students; (3) students visited a higher proportion of educational websites than their teachers; and (4) teachers visited a higher proportion of search pages than teacher candidates. Results may be useful for researchers (1) to better understand generational differences between groups; (2) to expand educational technology research to better include non‐pedagogical support tools for educators; and (3) to serve as a counterpoint for self‐report data on web resource frequency of use, which may provide different results.