Non-invasive concealed object detection, identification, and discrimination have been of interest to the research community for decades due to the needs to preserve infrastructures and artifacts, guarantee safe conditions for the detection and location of landmines, etc. A modern approach is based on the use of an unmanned aerial vehicle equipped with ground-penetrating radar, which has the advantage of not requiring direct contact with the ground. Moreover, high-resolution underground images are obtained by coherently combining measurements by using a synthetic aperture radar algorithm. Due to the complexity of the real scenario, numerical analyses have always been welcomed to provide almost real-time information to make the best use of the potential of such kinds of techniques. This paper proposes an analysis of the scattering from a zero-thickness perfectly electrically conducting disk buried in a lossy half-space surrounded by air and illuminated by a field generated by a Hertzian dipole located in the air. It is carried out by means of a generalized form of the analytically regularizing Helmholtz–Galerkin technique, introduced and successfully applied by the authors to analyze the plane-wave scattering from a disk and a holed plane in a homogeneous medium. As clearly shown in the numerical results, the proposed method is very effective and drastically outperforms the commercial software CST Microwave Studio 2023.