In a medium bowl, mix together the dry batter ingredients: all purpose flour, sugar, salt. and baking powder.
In a large bowl, whisk the two eggs. When thoroughly scrambled, add the vanillaextract, oil, and milk and mix until well combined.
Slowly introduce the dry ingredients into the wet. Once you’ve mixed all the ingredients into a uniform mixture, your simple waffle batter is complete! Set aside and continue making the filling and frosting
Make the Cinnamon Filling
In a medium bowl, use a hand mixer to combine the brown sugar,ground cinnamon and butter.
Add 2 tablespoons of milk and continue mixing. If your filling doesn’t seem to come together, add the third and final tablespoon of milk. See photos for the target filling consistency
When done, use the filling to fill a piping bag. I learned this cool trick using a tall glass to help fill the bag.
Set aside and continue making the frosting
Make the Cream Cheese Frosting
In a medium bowl, combine the cream cheese, butter, powdered sugar, and vanilla extract. Use a hand mixer to reach the proper frosting consistency.
Fill a piping bag using the same method. Set aside for use when cooking the waffle
Cook the Waffle
After heating your waffle iron, assemble your waffle! My first attempt I layered in this order: filling, batter, frosting, batter, filling. This produced a tasty but UGLY waffle. My second try, I layered batter, filling, batter then simply topped with the frosting. It came out much prettier but not quite as tasty.
Cook the waffle for 5-10 minutes until desired “doneness” is achieved. With the frosting and filling, the waffle is a bit wetter and heavier than a regular waffle so consider cooking for longer than a normal waffle.