This review discusses imaging modalities for fracture repair assessment, with an emphasis on pragmatic clinical and translational use, best practices for implementation, and challenges and opportunities for continuing research. Semiquantitative radiographic union scoring remains the clinical gold standard, but has questionable reliability as a surrogate indicator of structural bone healing, particularly in early-stage, complex, or compromised healing scenarios. Alternatively, computed tomography (CT) scanning enables quantitative assessment of callus morphometry and mechanics through the use of patient-specific finite-element models. Dual-energy X-ray absorptiometry (DXA) scanning and radiostereometric analysis (RSA) are also quantitative, but technically challenging. Nonionizing magnetic resonance (MR) and ultrasound imaging are of high interest, but require development to enable quantification of 3D mineralized structures. Emerging image-based methods for quantitative assessment of bone healing may transform clinical research design by displacing binary outcomes classification (union/nonunion) and ultimately enhance clinical care by enabling early nonunion detection.