Research on workplace fun has neither identified the processes through which its positive impact is achieved nor the mechanisms that facilitate it. In the present study we examined the protecting role of five workplace fun dimensions with regard to need for recovery from work, turnover intentions, and chronic social stressors and the mediating role of vigor, dedication and absorption (work engagement). We also explored workplace fun under conditions of high, medium and low trust. The study was a cross-sectional survey. Four hundred and thirty-three employed individuals working in various professions in Greece participated by filling in an online questionnaire. Convenience sampling was used. A series of hierarchical regression analyses and mediation and moderation analyses showed that work engagement dimensions (vigor, dedication, and absorption) mediate the impact of organic workplace fun and management support for fun on turnover intentions, chronic social stressors and need for recovery from work. A significant interaction effect of trust for the relationship between different types of workplace fun and the outcomes measured was found. Our study shows that the relationship of workplace fun with favorable outcomes can be explained by fluctuations in work engagement and is stronger when trust levels are sufficient.