Preheat your oven to 350 degrees F and line 2 cupcake pans with some cupcake liners.
Grab a bowl and mix the cake mix, oil, water, and eggs, then set it aside.
In a separate, smaller bowl, mix together the cinnamon and brown sugar and then set that bowl aside too.
Place about 2 tablespoons of cake batter into the bottom of each muffin cup. Sprinkle about a teaspoon of the brown sugar mixture on top of the batter. Add another spoonful of batter on top of the brown sugar, then one more small spoonful of brown sugar over each cupcake.
Use a toothpick to swirl the batter and cinnamon mixture.
Bake the cinnamon roll cupcakes for 17-20 minutes. Cupcakes are done when slightly golden and a toothpick comes out clean.
While you let the cupcakes completely cool, mix all the ingredients for the frosting and beat until fluffy. Consistency Tip - You can add more powdered sugar to stiffen the frosting, as needed. Or, if your frosting is a little thick, you can mix in 1 tablespoon of milk at a time until you reach the consistency you like.
Open your store-bought cinnamon rolls and unwrap each roll until you are left with your desired size. (I unrolled mine to make it half the size and then I re-rolled the outer parts to use for another cupcake. Since you'll be covering it with glaze, it doesn't have to be super pretty!)
Add all the ingredients for the glaze to a small bowl and beat until smooth. Add more milk to thin it out so it drips easier over the cinnamon roll topping.
Pipe your desired amount of frosting onto each cupcake, then top with a mini cinnamon roll and drizzle with glaze.
Serve your cupcakes with a tall glass of milk!