Humor styles have been shown to play a stress-moderating role when individuals encounter difficulties and stressful events, and they are also associated with job satisfaction and psychological health. However, little is known about how different humor styles uniquely buffer or exacerbate the impact of work stress on job-related and psychological outcomes in high-stress professions such as policing. This study investigated the moderating effects of humor styles on the relationships between perceived work stress, job satisfaction, and psychological well-being among 438 Taiwanese police officers. Participants completed the Humor Styles Questionnaire, a perceived work stress scale, and measures of life satisfaction, positive and negative affect, and depression. Results indicated significant moderating effects of aggressive and self-defeating humor. The interaction between perceived work stress and aggressive humor significantly predicted job satisfaction and positive affect: officers high in aggressive humor showed no significant associations, whereas those low or moderate in aggressive humor showed negative associations. Furthermore, the interaction with aggressive humor also negatively predicted life satisfaction and positively predicted negative affect and depression across all levels, with the steepest effects among officers low in aggressive humor. Similarly, self-defeating humor moderated the effects of work stress on job satisfaction, positive affect, and depression: officers high in self-defeating humor, perceived work stress did not significantly predict outcomes, while for those low or moderate in self-defeating humor, higher stress was linked to lower job satisfaction and positive affect, as well as greater depression. By contrast, affiliative and self-enhancing humor did not show significant moderating effects. These findings highlight the complex and differential functions of humor styles in occupational stress contexts. While some humor styles appear to buffer against the detrimental effects of stress, others may exacerbate vulnerability.