The aims: This study aims to elucidate workers’ compensatory accident insurance purchasing behavior, as well as proposing a model to explain the behavioral intentions of front-line workers to purchase compensatory accident insurance. The scope: The workers of the container terminal in the Kaohsiung port were used as the sample in this study. Methodology: A questionnaire survey was administered to collect workers’ perceptions of accident insurance. The analysis methods of EFA, CFA and SEM were employed for further analysis. Conclusions: According to a primary component factor analysis, three dimensions of insurance perception were found: perceived risk; perceived need for accident insurance; and perceived usefulness of accident insurance. The findings indicate that perceived risk, perceived need, and perceived usefulness of accident insurance positively affect the intention to purchase accident insurance. It is also found that perceived need constitutes the major factor affecting the intention of front-line workers to purchase accident insurance. However, perceived need is determined to play both a mediating and modulating role in the insurance behavior evaluation process model.