The Heart of Darkness Medal is one of three medals Alex Shepherd must find in the Otherworld version of his home. It is located under a cabinet on the second floor in the guest room, and is awarded "For permitting others to suffer." The medal is used to solve the Medal Puzzle, one of four puzzles that prevent Alex from leaving the house.
This medal likely references the grief Alex caused by accidentally killing his brother Joshua; Alternatively, it could reference the kidnapping and murder of Shepherd's Glen townspeople by the Order that occurred after Adam Shepherd failed to sacrifice Alex and fulfill the Shepherd Family Contract. "For Permitting others to Suffer" could also symbolise Alex's success in causing grief in his household after the death of his brother, and also for the suffering that Joshua faced during his final moments.
- The Heart of Darkness closely resembles a Purple Heart. The Purple Heart is a distinction awarded by the U.S. Military for those wounded or killed in battle, while the Heart of Darkness is awarded for allowing others to suffer.
- The Purple Heart could reference Joshua's death by drowning, as when the body is deprived of oxygen, the skin turns purple.