Background: Motor vehicle crashes (MVC) are associated with diminished mental health, and furthermore, evidence suggests the process of claiming compensation following an MVC further increases distress and impedes recovery. However, further research is required on why the compensation process is stressful. The aim of the current study is twofold. The first is to investigate whether the interaction with the insurance agency is associated with anxiety. The second is to explore qualitatively aspects of dissatisfaction with the compensation process. Methods: Participants (N = 417) were injured people involved in a compensation scheme after a motor vehicle crash (MVC) in New South Wales, Australia. Interviews were conducted by phone at 2, 12 and 24 months after the MVC. A suite of measures were used including compensation related measures, pain catastrophising and the anxiety/depressed mood subscale of the EuroQol. The association between predictors and anxiety/depressed mood as the dependent variable were analysed using forward logistic regression analyses. The comments about dissatisfaction with the insurance company were analysed qualitatively. Results: The strongest predictor of mood status found was pain-related catastrophising, followed by dissatisfaction with the insurance company. Dissatisfaction was attributed to (1) lack of communication and lack of information, (2) delayed or denied payments of compensation, (3) slow treatment approval and discussions about causality, (4) too much complicated paperwork, and (5) discussions about who was at-fault. Conclusions: Factors were found that contribute to anxiety in the compensation process. The association between catastrophising and anxiety/depressive mood suggests it is worthwhile further investigating the role of negative cognitions in compensation processes. People who score highly on catastrophising after the MVC may benefit from early psychological interventions aiming at addressing negative cognitions. Another important stressor is the interaction with the insurance company. Stress is associated with problems of communication, medical treatment, and claim settlement. This study additionally draws attention to some under recognised problems such as delayed payments. Pro-active claims management could address some of the identified issues, which could improve health of injured people after a MVC.