To make the waffles, in a medium bowl whisk together flour, cocoa powder, sugar, baking powder, salt, baking soda, and cinnamon. Whisk to combine.
In a small bowl beat eggs. Add butter, buttermilk, and vanilla extract and whisk well.
Add the wet ingredients all at once to the dry ingredients and whisk to combine, making sure the mixture is thoroughly incorporated and no lumps remain. Stir in the chocolate chips. Allow the batter to rest at room temperature for 10 minutes while the waffle iron heats up. This will thicken the batter a bit.
Heat the waffle iron, ladle the rested dough into the waffle, and cook according to your waffle machine.
When they’re baked to your desired doneness, remove from the waffle iron and let rest on a wire baking rack over a sheet pan. This will keep the underside from getting soggy. Keep the cooked waffles warm in a very low oven while you make the rest of the waffles. You’ll want to serve them all slightly warm.
To make the whipped cream, in a medium bowl combine cream, powdered sugar, salt and vanilla. Use an electric hand mixer on medium speed to beat the cream to soft peaks.
To make the the chocolate sauce, in a small saucepan over low heat, combine cocoa powder sugar, cream, butter and salt. Whisk until the butter is melted the cream is just simmering around the edges, and the mixture is glossy and smooth. Remove from heat and stir in vanilla extract. Pour into a small pitcher to serve. Chocolate sauce can be stored in the refrigerator and reheated in a small saucepan with a dash more cream.
To serve, dollop warm waffles with whipped cream, drizzle with chocolate sauce and enjoy!