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Simple Summary: Effective assessment of treatment response is essential for optimizing outcomes in cancer patients. This study examines how specific features derived from CT scans can accurately predict the effectiveness of preoperative chemotherapy in patients with carcinoma of the gastroesophageal junction. We found measurable differences in imaging data between patients with significant tumor regression and those with limited or no response. These findings highlight the potential for advanced imaging to enhance personalized treatment strategies and improve overall patient management. This research offers a new approach to personalized cancer care. Background: The purpose of this retrospective study was to evaluate the value of contrast-enhanced computed tomography (CE-CT) image features at baseline and after neoadjuvant chemotherapy in predicting histopathological response in patients with adenocarcinoma of the gastroesophageal junction (GEJ). Methods: A total of 105 patients with a diagnosis of adenocarcinoma of the GEJ were examined by CE-CT at baseline and preoperatively after neoadjuvant chemotherapy. All patients underwent surgical resection. Histopathological parameters and tumor regression grading according to Becker et al. were collected in 93 patients. Line profiles of the primary tumor area in baseline and preoperative CE-CT were generated using ImageJ. Maximum tumor density and tumor-to-wall density delta were calculated and correlated with the histopathological tumor response. In addition, tumor response was assessed according to standard RECIST measurements in all patients and by endoscopy in 72 patients. Results: Baseline and change in baseline to preoperative CE-CT parameters showed no significant differences between responders (Becker grade 1a, 1b) and non-responders (Becker grade 2, 3). After neoadjuvant therapy, responders and non-responders showed significant differences in maximum density and tumor-to-wall density delta values. Line profile measurements showed excellent inter-rater agreement. In comparison, neither RECIST nor endoscopy showed significant differences between these groups. Conclusions: Posttreatment CE-CT can predict histopathological therapy response to neoadjuvant treatment in adenocarcinoma of GEJ patients with high accuracy and thus may improve patient management. [ABSTRACT FROM AUTHOR]