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Prepare the pineapple cake mix according to package instructions using a 9×13 pan. Let cool slightly.
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Use the end of a wooden spoon to poke holes all over the warm cake.
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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.
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Let the cake cool completely, then spread the drained crushed pineapple evenly over top.
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Mix the rum extract into the whipped topping. Spread or pipe the whipped topping over the pineapple layer.
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Sprinkle the shredded coconut over the entire cake.
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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.