We explore the effects of retirement on both physical and mental ill-health and whether these change in the presence of economic shocks. We employ inverse probability weighting regression adjustment to examine the mechanisms influencing the relationship between retirement and health and a difference-in-differences approach combined with matching to investigate whether the health effects of retirement are affected by the Great Recession. We estimate these models on data drawn from the English Longitudinal Study of Ageing (ELSA) and find that retirement leads to a deterioration in both mental and physical health, however there seems to be considerable effect heterogeneity by gender and occupational status. Our findings also suggest that retiring shortly after the Great Recession appears to improve mental and physical health, although only among individuals working in the most affected regions. Overall, our results indicate that the health effects of retirement might be influenced by the presence of economic shocks.