This study examined whether the six trait-like dimensions of psychological well-being (e.g., autonomy and environmental mastery) moderate the effects of unemployment on various facets of subjective well-being (i.e., life satisfaction, satisfaction with life domains, and experienced mood). Further, re-employment expectations during unemployment were investigated as a moderator in this context. The study is based on monthly panel data ( Nobservations > 23,000) of two samples of initially employed German jobseekers, who either registered as jobseekers due to (i) mass layoffs or plant closures ( N = 552) or (ii) other reasons ( N = 988). The results indicate substantial interindividual differences in unemployment-related changes across all examined subjective well-being facets. However, dimensions of psychological well-being did generally not moderate these changes. Only in one unemployment context, environmental mastery was positively related to unemployment-related mood changes. Good re-employment expectations were related to increases in several well-being facets (e.g., leisure satisfaction) compared to being employed, whereas poor re-employment expectations were associated with particularly detrimental effects of unemployment in terms of life satisfaction. Overall, the study provides further evidence that (perceived) contextual features of unemployment seem to be particularly relevant for how individuals experience unemployment, whereas internal (coping) resources only seem to play a negligible role.