Step 1

First, make your cinnamon roll filling. In a medium bowl, combine the melted butter, brown sugar and ground cinnamon until incorporated. Mixture will be very runny, but as you make your cookie dough it will firm up. Set aside.

Step 2

For the cookie dough: In the bowl of a stand mixer, cream together the butter and sugar with the paddle attachment until creamy and pale yellow, about 2 minutes. Add in the egg, vanilla, and heavy cream and mix well. Lastly, add in the salt, baking powder, and flour and mix until a soft dough comes together. The dough will be soft and sticky. This will yield tender cookies!

Step 3

Lightly flour a clean workspace, such as your countertop. Alternatively you can lightly flour a large piece of parchment or wax paper. Place the dough onto the floured surface and use your hands to press it into a 10x15"ish size rectangle. It doesn't have to be exact; around a large rectangular size is what we're aiming for.

Step 4

Spread the dough with the filling, leaving about a 1/2 inch margin around the edges. Starting with the longest side closest to you, begin rolling the dough up into a log shape slowly, taking care to pinch together any tears in the dough along the way. It doesn't have to be neat or perfect! Once in the log shape, cut into 12 equal pieces with a sharp knife. Roll each piece into a dough ball and place on a parchment-lined baking sheet. Freeze the dough balls for at least 30 minutes.

Step 5

Preheat oven to 350° F. Line 2 baking sheets with parchment paper. Place 6 dough balls, roughly 2-3" apart on one of the baking sheets and bake for 15-17 minutes, rotating the pan halfway through baking time to ensure even cooking, or until cookies are light golden brown and appear set. Keep remaining dough balls in the freezer while the one tray bakes. This will maintain texture and prevent some spreading. Cool on the trays for about 15 minutes, then transfer to wire racks to cool completely.

Step 6

For the frosting: In a medium bowl, combine the cream cheese, butter, and vanilla with a handheld electric mixer until combined. Add in the confectioners' sugar and beat until combined. Spread the frosting over the cooled cookies.

Step 7

Store any cookies in an airtight container in the fridge.