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The art of light engineering unveils a world of possibilities through the meticulous manipulation of photonic properties such as intensity, phase, and polarization. Precision control over these properties finds application in a variety of fields spanning communications, light–matter interactions, laser direct writing, and imaging. Terahertz (THz) range, nestled between microwaves and infrared light, stands out for its remarkable ability to propagate with minimal losses in numerous dielectric materials and compounds, making THz imaging a powerful tool for noninvasive control and inspection. In this study, a rational framework for the design and optimal assembly of nonparaxial THz imaging systems is established. The research is centered on lensless photonic systems composed solely of high‐resistivity silicon‐based nonparaxial elements such as the Fresnel zone plate, the Fibonacci lens, the Bessel axicon, and the Airy zone plate, all fabricated using laser ablation technology. Through a comprehensive examination through illumination engineering and scattered light collection from raster‐scanned samples in a single‐pixel detector scheme, the imaging systems are evaluated via diverse metrics including contrast, resolution, depth of field, and focus. These findings chart an exciting course toward the development of compact and user‐friendly THz imaging systems where sensors and optical elements seamlessly integrate into a single chip. [ABSTRACT FROM AUTHOR]