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Anal cancer is a rare malignancy with an estimated 8,580 new cases each year in the USA where hematochezia, a common condition, is often the initial presenting sign. We describe a 51-year-old woman who presented with painful hematochezia, with a delayed diagnosis of anal cancer in the setting of missed and misdiagnosed digital rectal exams in an otherwise low-risk patient. This case highlights the importance of maintaining a broad differential diagnosis for hematochezia and the utility of thorough physical exams.