Aims: To describe an unusual case of retropharyngeal amyloidosis presenting with progressive dysphagia and dysphonia, and to highlight key clinical and radiologic features that assist in differentiating this rare entity from malignancy and other infiltrative processes. Methods: A 74-year-old man underwent clinical assessment and sequential investigations including barium swallow, contrast-enhanced CT neck, MRI neck, and targeted biopsy with immunohistochemistry. Imaging findings were evaluated for characteristics suggestive of infiltrative, inflammatory, or malignant pathology. Results: Barium swallow demonstrated a long segment of retropharyngeal thickening causing impaired bolus transit. CT revealed a hypodense (30 HU), minimally enhancing retro-pharyngeal lesion from C2–C6 with pharyngeal compression. MRI showed mixed T1/T2 signal, minimal enhancement, restricted diffusion, and preservation of the posterior fat plane—features suggestive of a non-destructive infiltrative process rather than malignancy. Biopsy confirmed amyloid deposition with positive Amyloid P and Amyloid A staining. Conclusion: Retropharyngeal amyloidosis is exceedingly rare and often mimics malignancy or other infiltrative conditions. Imaging may show diffuse, non-enhancing, non-destructive soft-tissue thickening with preserved fat planes, but findings are generally non-specific. Diagnosis relies on tissue confirmation. In older patients with slowly progressive dysphagia and atypical retropharyngeal lesions, the differential should include amyloidosis, as early recognition may prevent unnecessary aggressive intervention.