The high rates of training transfer failure that prevail still puzzle practitioners as well as researchers. The central aim of the present study is to analyze the relatively under-researched role of job dissatisfaction in the training transfer process. Specifically, we expect that job dissatisfaction would have a negative effect on transfer but that this effect would be buffered by the expectation of positive transfer consequences and motivation to transfer. To test these hypotheses, 220 participants in different training programs completed an online questionnaire 1 year after training. The results support our assumptions. They reveal that job dissatisfaction has a detrimental effect on training transfer, but that motivation to transfer and the expectation of positive transfer consequences have a buffering effect. The more motivated a person is towards transfer, the less negative is the effect of job dissatisfaction on actual transfer, but only if a person expects positive outcomes from transfer, such as acknowledgment or rewards. The findings are discussed in relation to existing training transfer models, as well as models of job (dis)satisfaction.