Preheat oven to 350°F. Line a baking sheet with parchment paper.

In two small bowls, prepare the streusel:

For the vanilla streusel, combine 2 tablespoons flour, 1 tablespoon cold butter, and 2 tablespoons vanilla pudding mix. Cut the butter into the mixture until crumbly.

For the strawberry streusel, combine 2 tablespoons flour, 1 tablespoon cold butter, and 2 tablespoons strawberry Jello mix. Cut the butter into the mixture until crumbly.

Spread each mixture on half of the prepared baking sheet.

Bake for 8-9 minutes until lightly toasted but not browned.

Cool completely, crumble both mixtures together, and set aside.

In a large mixing bowl, combine 1 box strawberry cake mix, 2 tablespoons flour, 1/4 cup oil, 2 eggs, and 2 tablespoons heavy cream.

Mix until fully combined and smooth.

Using a cookie scoop, portion the dough onto a parchment-lined baking sheet, spacing about 3 inches apart.

Bake at 350°F for about 9 minutes until centers are just set.

Cool completely on the baking sheets before frosting.

In a stand mixer, beat 3 oz softened cream cheese until smooth.

Add 1/4 cup powdered sugar and 3 tablespoons vanilla pudding mix; mix until combined.

Gradually add 1 1/2 cups heavy cream on low speed until combined. Increase speed to medium and whip until thick, smooth, and fluffy.

Transfer frosting to a piping bag fitted with a large star tip.

Pipe a swirl of frosting onto each cooled cookie.

Generously sprinkle with the prepared streusel topping.