The current working environment requires employees to have some control over their jobs. Drawing on the job demands–resource (JD-R) theory, we investigated the relationship between job crafting and job boredom. Based on the generational cohort theory, we determined the strength of the relationship using generational diversity as a moderator. Data from 320 participants employed in white-collar jobs in the private sector were collected over two time periods. Structural equation modeling and hierarchical regression were used in the analysis. The results of this study show that job crafting has a significant negative impact on job boredom. This effect is further differentiated by generational differences, that is, belonging to Gen X or the Millennial cohorts. The use of self-administered questionnaires may result in the selection of ‘socially desired’ outcomes. This study has implications for today’s intergenerational environment, since different generational groups have different attributes, priorities, desires and motivations that impact their actions. This study adds to the limited research on the impact of job crafting on job boredom. However, this is the first study to examine the moderating effect of Gen X and Millennials on the relationship between job crafting and boredom. As a result, appropriate incentives can be implemented to encourage crafting among generational cohorts within organizations, especially with the entry of Generation Z into the workforce.