Parathyroid imaging has significantly improved over recent decades, affecting the surgical approach from traditional bilateral neck exploration to targeted, focused, and minimally invasive approaches. However, critical unmet needs persist in parathyroid imaging that significantly impact clinical decision-making and surgical outcomes in primary hyperparathyroidism (pHPT) management. This chapter examines the persistent diagnostic challenges of various imaging modalities, from first-line techniques to other advanced molecular and morphological imaging approaches. Historically established first-line imaging modalities, including [99mTc]Tc-MIBI single photon emission tomography/computed tomography (SPECT/CT) and cervical ultrasonography (cUS), demonstrate substantial limitations in detecting multiglandular disease, with sensitivity dropping from 88% for single adenomas to as low as 26.7–61% for multiple gland involvement. The challenge of localizing ectopic parathyroid glands by conventional approaches is present in approximately 20% of treatment-naive patients and up to 66% in reoperative scenarios. Discordant imaging results between modalities create additional diagnostic uncertainty, potentially misdirecting surgical planning and compromising patient outcomes. Advanced imaging techniques, particularly [18F]fluorocholine positron emission tomography/ computed tomography (PET/CT), which is increasingly used as a first-line imaging modality today, offer superior diagnostic performance with patient-based sensitivities exceeding 95%. It demonstrates particular strength in challenging clinical scenarios where conventional imaging fails. Standalone CT with late-arterial phase imaging has remarkably good potential for detecting diseased parathyroid glands. 4D-CT, which relies on dynamic contrast enhancement patterns, may be considered if appropriate nuclear medicine techniques are unavailable and both ultrasound and late-arterial phase CT yield inconclusive results. However, it comes at the expense of significant radiation exposure. Artificial intelligence applications show some promise for addressing some of the current limitations. Differentiating parathyroid carcinoma from benign lesions remains one of the greatest challenges in endocrine imaging, as substantial overlap in imaging characteristics across all modalities necessitates multimodal clinical correlation. Cost-effectiveness considerations and the limited availability of advanced imaging technologies further influence their clinical implementation. Recognizing these unmet needs is essential to drive both technological innovation and improvements in clinical practice.