Sift flour, 3 tablespoons sugar, baking powder, 1 teaspoon cinnamon, and salt into a large bowl.
Whisk milk, egg, melted butter, and vanilla in a separate container until emulsified.
Fold the wet ingredients into the dry ingredients until a thick batter forms, avoiding over-agitation of gluten.
Combine the coating sugar and 2 teaspoons cinnamon in a shallow pan and set aside.
Heat 1 tablespoon of oil in a heavy-bottomed skillet over medium heat until shimmering.
Deposit 0.25 cup of batter per pancake into the skillet, cooking for 2-3 minutes until the periphery is set and bubbles persist.
Flip the pancakes and cook for an additional 2 minutes until the internal temperature reaches 190 degrees Fahrenheit.
Immediately transfer the hot pancakes to the cinnamon-sugar pan and coat all surfaces thoroughly.
Heat heavy cream to a simmer and pour over chocolate pieces, allowing to sit for 2 minutes before whisking into a smooth ganache.
Stack the coated pancakes and serve with the warm chocolate ganache for dipping.