Adenosquamous carcinoma (ASC) of the gallbladder is an incredibly rare malignancy. It is much less common than adenocarcinoma of the gallbladder and also has a much poorer prognosis. The case presented here is that of a patient diagnosed with ASC of the gallbladder after undergoing cholecystectomy for symptomatic cholelithiasis. Her disease progressed despite four cycles of chemotherapy. Her course was complicated by recurrent obstructive jaundice requiring biliary duct stent placement and percutaneous biliary drain placement over several admissions. She was discharged home with hospice service seven months after diagnosis, where she died a few weeks later. Knowledge pertaining to gallbladder ASC is limited, as prevalence is low and information is mostly derived from case reports such as this.