We present a case of a 51-year-old female with a history of acquired immunodeficiency syndrome (AIDS) and medication non-compliance who experienced progressively worsening dysphagia to both solids and liquids over a three-month period. The patient underwent an esophagogastroduodenoscopy (EGD), which revealed multiple small pseudodiverticula without any other notable abnormalities. Subsequently, a barium esophagogram was performed, confirming the presence of multiple esophageal pseudodiverticula. Biopsies taken during the procedure showed chronic inflammatory changes, with no evidence of viral or fungal elements. In light of the patient's HIV history and the absence of esophageal candidiasis, the diagnosis of esophageal intramural pseudodiverticulosis (EIP) was made. The patient was initiated on highly active antiretroviral therapy (HAART) and received high-dose proton pump inhibitors (PPIs). Remarkably, the patient reported a complete resolution of her dysphagia symptoms during the follow-up visit. Risk factors associated with EIP include HIV infection, diabetes mellitus (DM), and esophageal candidiasis. To confirm the diagnosis, a barium esophagogram is considered the preferred imaging study. The management of EIP focuses on PPI therapy, the dilation of strictures if present, and addressing the underlying etiology. Given the association between EIP and esophageal malignancies, surveillance endoscopy may be recommended in these patients. This case highlights the importance of considering EIP as a potential cause of dysphagia, particularly in individuals with HIV/AIDS, even in the absence of esophageal candidiasis. Prompt diagnosis and appropriate management can lead to symptom resolution and improved quality of life for affected patients.