Preheat your oven to 350°F and line a baking sheet with parchment paper. In one small bowl, combine 5 tbsp flour, 2.5 tbsp softened butter, and 2 tbsp strawberry jello powder, mixing until the texture resembles coarse breadcrumbs. In another small bowl, repeat the same process with 2 tbsp flour, 2.5 tbsp softened butter (you'll need 5 tbsp total butter, so use 2.5 tbsp per mixture), and 2 tbsp vanilla pudding powder. Spread both crumble mixtures separately on the prepared baking sheet and bake for 11 minutes until lightly golden and fragrant. Remove from oven and let cool completely, then gently break apart and combine both crumbles in a small bowl—this gives you a strawberry-vanilla crumble topping.

In a large mixing bowl, combine the strawberry cake mix, 2 tbsp all-purpose flour, 1/4 cup oil, 2 large room-temperature eggs, and 3 tbsp heavy cream. Mix until just combined—don't overmix, as this will keep your cookies tender. The batter should be thick and slightly textured. I find that room temperature eggs blend more smoothly into the batter, creating a better crumb structure in the final cookie.

Using a cookie scoop or spoon, portion the dough into 8 evenly-sized balls and place them on a fresh parchment-lined baking sheet, spacing them about 2 inches apart. Bake at 350°F for 9 minutes until the edges are set but the centers still look slightly underdone—they'll continue cooking as they cool. This ensures a soft, cake-like texture rather than a crispy cookie.

Remove the baking sheet from the oven and let the cookies cool on the pan for 15 minutes—this allows them to set and become sturdy enough to handle without breaking, while still staying soft inside. After 15 minutes, you can transfer them to a cooling rack if desired, but they're sturdy enough to frost directly on the pan.

While the cookies cool, prepare your frosting. Start by beating 3 oz softened cream cheese in a medium bowl until smooth and creamy, about 30 seconds. Add 1.5 cups cold heavy whipping cream, 3.5 tbsp vanilla pudding mix, and 1/3 cup sifted powdered sugar. Whisk everything together for about 60 seconds until the frosting reaches stiff peaks and has a fluffy, mousse-like texture. I like to sift the powdered sugar first to avoid lumps that can break down the whipped texture.

Once the cookies are completely cooled, generously frost each one with the whipped cream cheese frosting using a piping bag or offset spatula. Top each frosted cookie with a spoonful of the combined strawberry-vanilla crumble mixture from Step 1, pressing it gently into the frosting so it adheres. Serve immediately or chill until ready to eat—these cookies are best enjoyed fresh, within a few hours of assembly.