Prepare the pineapple cake mix according to package instructions using a 9×13 pan. Let cool slightly.
Use the end of a wooden spoon to poke holes all over the warm cake.
In a bowl, whisk together the coconut pudding mix and milk. Pour over the poked holes in the cake, allowing it to seep into the holes.
Let the cake cool completely, then spread the drained crushed pineapple evenly over top.
Mix the rum extract into the whipped topping. Spread or pipe the whipped topping over the pineapple layer.
Sprinkle the shredded coconut over the entire cake.
Refrigerate for at least 4 hours before slicing and serving.
For a boozy version: Reduce milk in pudding mixture to 1 1/2 cups. Add 1/2 cup rum and mix into the pudding before pouring over cake.
This easy poke cake brings all those nostalgic piña colada flavors together in a fun, creamy, tropically-inspired dessert! Perfect for spring and summer parties.