Ingredients
For the crust:
Cooking spray
- 18
vanilla sandwich cookies, such as Golden Oreos (about 7 1/2 ounces)
- 1/2 cup
toasted sweetened, shredded coconut
- 1/4 teaspoon
kosher salt
- 3 tablespoons
unsalted butter, melted
For the cream cheese layer:
- 5 ounces
cream cheese, at room temperature
- 3/4 cup
powdered sugar
- 1 tablespoon
white rum (optional)
- 1/4 teaspoon
kosher salt
- 1 1/4 cups
cold heavy cream
- 1 cup
toasted sweetened, shredded coconut
For the pudding layer:
- 1/2 cup
cold heavy cream
- 1 (20-ounce) can
crushed pineapple in 100% juice
- 1 tablespoon
finely grated lime zest (1 to 2 medium limes)
- 4 teaspoons
freshly squeezed lime juice (1/2 medium lime)
- 1 (3.4-ounce) box
instant vanilla pudding mix
For the whipped cream and garnish:
- 1 cup
cold heavy cream
- 3 tablespoons
powdered sugar
- 1 tablespoon
white rum (optional)
- 1/4 teaspoon
vanilla extract
- 1/3 cup
toasted sweetened, shredded coconut
- 16
maraschino cherries, for topping (optional)
Make the crust:
Lightly coat an 8-inch square baking pan (at least 2 inches high) with cooking spray. Line the pan with 2 sheets of parchment paper positioned perpendicular to each other so that there is parchment overhanging on all sides. Lightly spray cooking spray between the sheets if needed to keep the paper in place.
Process 18 vanilla sandwich cookies, 1/2 cup of the toasted coconut, and 1/4 teaspoon kosher salt together in a food processor, stirring a few times, until the cookies are broken down into fine crumbs, about 1 1/2 minutes total. Drizzle with 3 tablespoons melted unsalted butter and pulse until evenly moistened and the mixture clumps when squeezed, about 5 (1-second) pulses.
Transfer to the baking pan and use the bottom of a flat measuring cup to press the crust into an even layer. Freeze while you prepare the cream cheese layer.
Make the cream cheese layer:
Beat 5 ounces room-temperature cream cheese, 3/4 cup powdered sugar, 1 tablespoon white rum if using, and 1/4 teaspoon kosher salt in a stand mixer with the whisk attachment on medium speed until smooth and combined, scraping down the sides of the bowl as needed, about 1 minute.
Reduce the speed to medium-low. Slowly pour in 1 1/4 cups cold heavy cream. Increase the speed to medium-high and beat, scraping the bowl as needed, until stiff peaks form, 30 seconds to 1 minute.
Fold in 1 cup of the toasted coconut with a flexible spatula until evenly distributed. Spoon over the crust and spread into an even layer. Refrigerate while you make the pudding.
Make the pudding layer:
Beat 1/2 cup cold heavy cream in the stand mixer (no need to clean) with the whisk attachment on medium-high speed, scraping as needed, just until stiff peaks form, 1 to 3 minutes. Transfer to a small bowl.
Drain 1 (20-ounce) can crushed pineapple into a liquid measuring cup or bowl until you’ve drained out 1/2 cup juice.
Place the remaining pineapple and juice in the stand mixer (no need to clean). Add 1 tablespoon lime zest, 4 teaspoons lime juice, and 1 tablespoon of the reserved pineapple juice. Sprinkle 1 (3.4-ounce) box instant vanilla pudding mix over the pineapple and stir with a flexible spatula until combined. Fold in the whipped cream until well-combined.
Spoon over the cream cheese layer and spread into an even layer. Refrigerate while you make the whipped cream.
Make the whipped cream and finish:
Beat 1 cup cold heavy cream, 3 tablespoons powdered sugar, 1 tablespoon white rum if using, and 1/4 teaspoon vanilla extract in the stand mixer (no need to clean) with the whisk attachment on medium-high speed just until stiff peaks form, 1 to 3 minutes. Spoon over the pudding in an even layer and smooth or swoop over the top as desired.
Loosely cover with plastic wrap. Refrigerate until well-chilled and set, at least 5 hours and up to overnight. (If chilling overnight, store the remaining toasted coconut in an airtight container at room temperature.)
When ready to serve, sprinkle the remaining 1/3 cup toasted shredded coconut over the top. Grasping the excess parchment, lift the slab out of the pan and place on a cutting board. Cut into 16 pieces, wiping the knife between each cut for the cleanest-looking slices. Garnish each slice with a maraschino cherry if desired.

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