On January 28, 2023, at 1751 central standard time, an Aero Commander 500-B, N107DF, was substantially damaged when it was involved in an accident near Sylacauga, Alabama. The pilot was seriously injured. The airplane was operated as a Title 14 Code of Federal Regulations Part 91 positioning flight. According to the pilot, he flew a different airplane to the Tampa Executive Airport (VDF), Tampa, Florida, and intended to reposition the accident airplane, which was due for a 100-hour inspection, to Birmingham-Shuttlesworth International Airport (BHM), Birmingham, Alabama, for maintenance. During the preflight inspection, the pilot turned on electrical power and noticed that the fuel gauge was reading 80 gallons of fuel. He walked into the FBO at VDF and requested that the airplane’s fuel tanks be topped off. A ramp technician reported that the fuel tanks were already full. The pilot subsequently removed the airplane’s fuel cap, noticed fuel in the filler neck and assumed the fuel tanks were full. He did not push open the anti-siphon fuel valve to see if the tanks were full. The pilot reported the airplane holds a maximum of 156 gallons of fuel and he calculated that he needed 113 gallons of fuel to legally complete the flight. According to the fueler at the FBO, she removed the airplane’s single fuel cap and saw fuel on top of the anti-siphon valve. She used her finger to push down the valve and felt fuel, so she believed the airplane was full of fuel and it did not need additional fuel. The pilot completed the preflight inspection checklist and started the engines. He noticed the fuel gauge was flickering and thought it was malfunctioning. He proceeded to depart for BHM. After about 2 hours of flight time, the airplane’s right engine lost power and, a few seconds later, the left engine also lost power. He did not look at the fuel gauge during this time. He notified the air traffic controller of the loss of power to both engines and was vectored towards Merkel Field Sylacauga Municipal Airport (SCD), Sylacauga, Alabama. The airplane was unable to reach the runway and the pilot performed a landing in a cotton field. After landing, the airplane rolled into trees and the left wing separated from the fuselage. Federal Aviation Administration inspectors who examined the airplane at the accident site noted the airplane sustained substantial damage to the left and right wings. They also noted that both wing fuel bladders were breached and noted minor fuel leakage on the ground adjacent to the wing. Personnel with the wreckage recovery company stated that there was no fuel in the airplane’s fuel tanks at the accident site. When electrical power was applied to the airplane, the fuel gauge read 68 gallons of fuel. The fuel transmitter was sent to the manufacturer for examination. Testing of the transmitter revealed no anomalies with the unit.