Constructing self‐repairing epoxy materials based on transesterification chemistry can be regarded as a potential path for practical industrial applications given on its simplicity and ease of processing. However, there is still a challenge to improve the slow bonding exchange process for desired healing performances. Herein, this work reports a simple and effective strategy to prepare high‐biomass‐content self‐repairing epoxy materials by introducing polyester oligomer (PEO) dicarboxylic acid as modifier into epoxidized soybean oil and itaconic acid compounds. The PEO is synthesized from glutaric anhydride and 1,4‐cyclohexanediol, as well possess a unique pentamer molecular structure. It not only endows the epoxy system with improved molecular mobility in virtue of its long‐chain structure, but also increases the number the essential ester groups of transesterification process, thus synergistically promoting bonding exchange rate for expected properties. As a result, the employment of PEO decreases the activation energy from 100 to 70 KJ/mol, as well as presents optimized self‐repairing efficiency in storage modulus and tensile strength tests compared to the control group. It may provide a new and practical way to fabricate high‐effective self‐repairing epoxy system for industrial applications. Description of preparation of bio‐based epoxy system with desired self‐repairing performance, and the mechanism for improved self‐repairing properties.