Preheat your oven to 350°F (175°C) and line your baking sheets with parchment paper.

Cream together 1 cup of softened unsalted butter, 1/2 cup of granulated sugar, and 1 cup of brown sugar until light and fluffy.

Add in 2 room-temperature eggs and 1 tablespoon of vanilla extract, mixing until well combined.

In a separate bowl, whisk together 3 cups of all-purpose flour, 1 cup of crushed graham crackers, 1 teaspoon baking powder, 1 teaspoon baking soda, and a pinch of salt.

Gradually add the dry mixture into the wet ingredients, mixing at low speed until just combined.

Using a 2-inch cookie scoop, portion out the cookie dough onto the prepared baking sheets.

Bake for 8-10 minutes, or until the edges are golden brown. Let cool for 5 minutes before transferring to a wire rack.

For the frosting, cream together 1/2 cup of softened butter, 8 ounces of cream cheese, and 1 teaspoon of vanilla extract.

Gradually incorporate 2 cups of powdered sugar until reaching a fluffy consistency.

Combine 1 cup of brown sugar, 1/2 cup of butter, and 1/2 cup of heavy whipping cream in a saucepan, stirring over medium heat until thickened.

Pipe a swirl of frosting on each cooled cookie and drizzle with caramel before serving.