Prepare the Cookies:

• Preheat your oven to 350°F (175°C).
• In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
• Add the egg and vanilla extract, mixing until fully incorporated.
• In a separate bowl, whisk together the all-purpose flour, cocoa powder, baking soda, baking powder, and salt.
• Gradually add the dry ingredients to the wet ingredients, mixing until just combined.
• Scoop out 2-tablespoon-sized balls of dough and flatten them slightly with your hands. Place them on a baking sheet lined with parchment paper, spaced about 2 inches apart.
• Bake the cookies in the preheated oven for 8-10 minutes, or until the edges are set but the centers are still soft.
• Remove from the oven and let them cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.

Prepare the Cheesecake Filling:

• While the cookies cool, beat the softened cream cheese, granulated sugar, and vanilla extract together in a bowl until smooth and creamy.
• Transfer the mixture to a piping bag or a ziplock bag with the corner snipped off for easy filling.

Prepare the Strawberry Filling:

• Take your hulled strawberries and slice off the tops, creating a flat surface.
• With a small knife, hollow out the center of each strawberry slightly to create space for the cheesecake filling.

Assemble the Cookies:

• Take one cooled cookie and pipe a small amount of cheesecake filling onto the flat side.
• Press a prepared strawberry onto the filling, flat side down, so the cheesecake filling oozes into the hollowed center of the strawberry.
• Pipe more cheesecake filling around the base of the strawberry, covering it completely.

Prepare the Cheesecake Frosting:

• In a large bowl, beat together the softened cream cheese and butter until smooth.
• Gradually add the powdered sugar, beating until light and fluffy.
• Add the vanilla extract and continue beating until smooth.
• If the frosting is too thick, add 1-2 tablespoons of heavy cream to achieve your desired consistency.

Frost the Cookies:

• Transfer the cheesecake frosting to a piping bag fitted with a round tip.
• Pipe a generous amount of frosting on top of each assembled cookie, covering the cheesecake-stuffed strawberry.
• Optionally, sprinkle a pinch of ground cinnamon over the frosting for extra flavor.