Postoperative headaches (POHs) following retrosigmoid microsurgery for vestibular schwannoma (VS) can significantly impact patients’ perceived health benefits (PHBs). In this cross-sectional observational study, 101 VS patients were investigated. For the assessment of pain, the Rostock Headache Compendium (RoKoKo) and the German pain processing questionnaire (FESV) were used. The perceived health benefits (PHBs) were assessed by the Glasgow Benefit Inventory (GBI) and Big Five personality traits were measured using the Ten-Item Personality Inventory (TIPI-G). We showed that 55% of the participants experienced POHs, leading to a marked reduction in overall PHBs compared to those without POHs. The correlation analysis revealed an association between decreased PHBs and elevated levels of pain-related helplessness, depression, anxiety, and anger. Positive correlations were identified between PHBs and action-planning competence, cognitive restructuring, and the experience of competence. Low emotional stability and openness yielded associations with pain-related psychological impairment. Hearing loss and facial paresis did not exert a significant impact on PHBs. The study highlights the influence of pain-related coping strategies on PHBs in long-term POH patients. Thus, coping mechanisms and personality traits should be assessed even before surgery for post-surgery pain prevention. The limitations of this study include a relatively small sample size, potential biases introduced by the overrepresentation of female patients, and the use of an online survey methodology. In conclusion, this research highlights that the interplay between headaches, PHBs, and psychological factors is also relevant in VS patients undergoing microsurgery. Short-term psychological interventions should therefore be taken into account to improve post-surgery adaptive coping strategies.