Older workers throughout Europe are increasingly expected to participate longer in the labour market. While training appears to increase workers’ employability, prior research indicates that employers are less prone to provide training with increasing age of the workers. In this study, we aim to provide a better understanding of what affects employers’ considerations. We conduct a vignette experiment among Dutch employers to investigate how the government and workers themselves can exert influence on employers’ willingness to provide training. Our analyses show that employers’ provision of training declines with workers’ age, and additionally reveal two mitigating mechanisms. First, government reimbursements appear to work as a buffer: when reimbursements are offered, the decline in employers’ willingness to offer training is less pronounced throughout workers’ careers. Second, workers’ interest in training has a delaying effect: when workers are interested in training, employers’ willingness to provide training remains rather stable until workers are aged about 55, and decreases only afterwards. This contrasts the constant decline with age when workers had no interest in training. Our findings emphasise that employers’ considerations cannot be understood without taking the context into account, because governments and workers can affect employers’ decisions through cost reduction and social exchange relations, respectively. More research is needed to disentangle other possible underlying mechanisms.