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Preheat oven to 350°F. Line a baking sheet with parchment paper.
In a large bowl, cream butter and sugar by beating for 2-3 minutes. Add the eggs and vanilla, then beat again, stopping to scrape the bottom and sides of the bowl.
Add the flour, baking powder, baking soda, salt, and cinnamon. Mix until combined, scraping the bottom and sides of the bowl.
Scoop large scoops of cookie dough onto the prepared baking sheet, spacing them a couple inches apart. Flatten them slightly by pressing down on the top of each bowl with your hand or a flat-bottomed cup until they are approximately 3/4-inch thick.
Bake for 10-12 minutes until set, but do not overbake. Cool completely.
Combine the butter, brown sugar, and cinnamon in a small saucepan. Cook over medium-high heat until the butter is melted and the mixture comes to a boil, then remove from the heat and spoon 2-3 teaspoons of the mixture over each cookie. Let cool. (See notes for microwave approach.)
In a large bowl, beat the cream cheese and butter until creamy and smooth. Add the milk, vanilla, and salt, then beat again. Add the powdered sugar, 1 cup at a time, mixing between each addition until smooth, about 1 minute.
Transfer the frosting to a piping bag fitted with a round open tip or a Ziploc bag with one corner cut off. Pipe thick spiral ropes of frosting on top of each cookie once the cinnamon sugar topping has cooled.