The legislative system of Taiwan’s Insurance Act is originated from the civil law system and the common law system. The Insurance Act allows the applicant and the insured can be two separate beings. The applicant can sign an insurance contract with the insurer upon other’s interests without his authorization. As a result, the person obligated to pay the premium can be different from the one enjoying the claim benefits of the contract. Because the use of the two legal systems tangled, the conflict is inevitable when Insurance Act is applied to the right and obligation between the applicant and the insured. Since the common law system and the civil law system are general concepts, this article focuses on representative cases of German Insurance Contract Law and Anglo-American Insurance Law. I clarify Taiwan’s Insurance Act is more similar to Germany legislation in essence. They both regulate the applicant as one of the parties. Based on that, I discuss the applicant’s duty to pay premium and the insured’s right to claim benefits, the possessing of insurable interest and the right to assign beneficiary. Finally, the relevant provisions of the applicant and the insured will be interpreted under the framework of existing legislation and suggestions of proper interpretation are offered.