Contractors help the government in carrying out construction and service projects. To reduce the risks resulting from the preparation and implementation of construction projects, the insurance industries should cooperate to include risk management. Contractors are facing many challenges regarding their insurance. Therefore, in this study, significant attention has been paid to identifying and ranking the challenges of contractor insurance in construction projects. The required information has been collected through the Delphi method and the opinions of experts in contracting companies. To identify the challenges, an open-ended questionnaire was distributed among the experienced insurance officials and 38 challenges have been identified. The relevant challenges formed the basis of a closed-ended questionnaire and the respondents were asked to re-evaluate their accuracy. Then, the approved challenges were the basis of the fuzzy best-worst method for weighing and ranking the related challenges. The results showed that the failure to provide specific consultation to contractors regarding the legal obligations of social security is the most important challenge in the field of contract insurance.