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Background/Aims: The incidence of morbid obesity has exponentially increased over the last decades. Bariatric surgery (BS) has been proven effective in inducing weight loss and resolving comorbidities associated with morbid obesity. However, BS can also lead to major diagnostic and treatment challenges in patients who develop upper gastrointestinal malignancies. It is important to create awareness of this rising problem. Methods: Relevant literature was searched in PubMed. Results: (Formerly) obese patients are more prone to develop upper gastrointestinal malignancies, mainly adenocarcinoma of the distal esophagus, since obesity induces a chronic pro-inflammatory state due to endocrinological changes. When an upper gastrointestinal malignancy develops after BS, diagnosis is often delayed and challenging due to a different presentation of complaints and the altered anatomy following the earlier surgery. Also, a potentially curative resection is often more complex and reconstruction of the gastrointestinal continuity can be seriously hampered. Conclusion: Due to the growing incidence of obesity and the increasing number of bariatric surgical procedures that are performed each year, it is expected that over the years to come, more post-BS patients will be diagnosed with upper gastrointestinal malignancies, providing great diagnostic and treatment challenges. Clinicians should be aware of this rising problem.