The capacity to find humorous perspectives in aversive situations may outline a helpful strategy in the context of cognitive reappraisal. Yet, research suggested that some people produce more adaptive humour than others. At the same time, not all forms of cognitive reinterpretation seem to be unequivocally beneficial. The present study aimed to investigate specific cognitive reappraisal strategies that individuals employ in humorous reappraisal of adverse events. In a sample of 95 participants, the use of cognitive reappraisal sub-strategies was assessed in a behavioural test in which participants were required to generate a series of humorous reappraisals of self-relevant, threatening events. These reappraisal sub-strategies (three positive reinterpretation strategies, three de-emphasising strategies) were then related to the habitual use of different kinds of humour as well as the broader DSM-5 personality trait domains and well-being in terms of depressive experiences, assessed by self-report questionnaires. While no robust relationships were found for reappraisal strategies based on de-emphasising, sub-strategies within the positive reinterpretation category showed specific and contrasting associations with the examined traits. Findings indicated that the ability to produce humour is only linked to a favourable pattern of reappraisal strategies when manifested in benign forms of humour. Specific relations also emerged for the broader personality traits. The study suggests that some characteristics that advance the use of benign humour also benefit adaptive emotion regulation. The opposite seems to be true for malicious, or "dark" humour. The introduced behavioural approach to the analysis of humorous cognitive reappraisal may prove useful also in future related research.