In a mixing bowl, stir together the flour, baking powder, salt, and cinnamon until fully combined. Set this bowl aside while you work on the wet ingredients. Keeping the dry mix separate at first helps everything blend evenly later.
Scoop about a cup of ice cream into a microwave-safe bowl. Heat it in short bursts of 15 to 20 seconds until it turns soft and pourable but not completely melted into liquid. This gentle approach protects any mix-ins so they stay intact in the batter.
In a larger bowl, whisk together the softened ice cream, eggs, milk, oil, and vanilla extract until smooth. The mixture should look creamy and slightly thick. This forms the flavorful base that gives the waffles their signature sweetness.
Gradually add the dry ingredients into the wet mixture, folding gently with a spatula. Stop as soon as the flour disappears into the batter. A few small lumps are completely normal and won't affect the final texture.
Preheat your waffle iron according to its instructions, then lightly coat it with non-stick spray. A properly heated iron is what gives waffles that golden crust instead of a pale, soft exterior. Give it a few extra minutes if you're not sure it's fully warmed up.
Pour about ¾ cup of batter onto the hot iron, close the lid, and cook for 3 to 4 minutes. Check for a deep golden color before removing each waffle. Repeat with the remaining batter until it's all used up.
Once the waffles have cooled slightly, use a knife to cut one into a cone shape and slice circles from another. Arrange the pieces on a plate to resemble an ice cream cone. Top with whipped cream, banana slices, sprinkles, a scoop of ice cream, and a cherry.