It is known that family breakdown and divorce are stressful for all parties. There is evidence these can even lead to suicide, especially in men. However it is not known how much various factors – such as child access restrictions and family court issues – cause stress, and whether the levels of stress change over time. The present study surveyed the experiences of 29 men who had separated from their partners. Participants submitted multiple reports (n = 408 for the whole sample) over a 12-month period. It was found that these reports included 358 stressful experiences related to child access problems, and 229 stressful experiences related to family court issues. Men’s mental well-being, measured using the Positive Mindset Index, was continuously low – just above clinical levels on average – throughout the 12-month period. Mental well-being was strongly negatively correlated to problems with child access (rs = –.571) and family court issues (rs = –.448). These correlations can be interpreted in the context of free text responses, which indicate that child access issues and family court issues had a negative impact on men’s mental well-being. Physical health problems were frequently reported too. Implications of these findings for the long-term mental health and physical health of men experiencing family breakdown are discussed in relation to the need for the family courts, and associated services, to recognise the chronic stress experienced by many men who find themselves in this predicament, and to ensure that court processes are resolved as swiftly as possible.