In a heavy bottom pan, melt chocolate and butter on low heat. Once completely melted, stir in sugar and set aside.
In a large mixing bowl, whisk eggs with milk and vanilla extract.
Slowly add the chocolate mixture into the milk mixture, stirring constantly until well-combined.
In a small bowl, combine flour, cacao powder, and baking powder.
In small portions, add the flour mixture to the chocolate mixture to make the batter.
Spoon the waffle batter into the waffle maker until each hole is completely filled. Cook until the outside is perfectly crispy.
Serve chocolate waffles warm with fresh berries, jam, or syrup, or freeze the leftover waffles for a busy morning. Alternately, serve the waffles with a scoop of vanilla ice cream for a fun dessert.