Ground-penetrating radar (GPR) has emerged as a prominent tool for imaging internal defects in cylindrical structures, such as columns, utility poles, and tree trunks. However, accurately reconstructing both the shape and permittivity of the defects inside cylindrical structures remains challenging due to complex wave scattering phenomena and the limited accuracy of the existing signal processing and deep learning techniques. To address these issues, this study proposes a migration-assisted deep learning scheme for reconstructing the shape and permittivity of defects within cylindrical structures. The proposed scheme involves three stages of GPR data processing. First, a dual-permittivity estimation network extracts the permittivity values of the defect and the cylindrical structure, the latter of which is estimated with the help of a novel structural similarity index measure-based autofocusing technique. Second, a modified Kirchhoff migration incorporating the extracted permittivity of the cylindrical structure maps the signals reflected from the defect to the imaging domain. Third, a shape reconstruction network processes the migrated image to recover the precise shape of the defect. The image of the interior defect is finally obtained by combining the reconstructed shape and extracted permittivity of the defect. The proposed scheme is validated using both synthetic and experimental data from a laboratory trunk model and real tree trunk samples. Comparative results show superior performance over existing deep learning methods, while generalization tests on live trees confirm its feasibility for in-field deployment. The underlying principle can further be applied to other circumferential GPR imaging scenarios. The code and database are available at: https://github.com/jwqian54/Migration-Assisted-DL.