This study combines two recognized theoretical frameworks in the (un)employment literature – the latent deprivation model and the vitamin model – and aims to better understand the relations between the perceived quality of the psychosocial environment and psychological well-being in older adults. The sample comprised 300 Portuguese adults (aged between 40 and 65), grouped as employed, unemployed engaged in training and unemployed not in training. The employed reported better well-being than the other groups, and the unemployed in training showed lower distress than those who were not. Additionally, features from both frameworks were found to be related to well-being. These findings highlight the merit of taking both theories into account to better understand the well-being of older individuals, and may be useful for the design of interventions aiming to enhance well-being and overcome some of the negative aspects of unemployment.