Prepare the Crust: In a medium bowl, combine graham cracker crumbs and sugar. Add melted butter and stir until the mixture resembles wet sand. Press this mixture evenly into the bottom and up the sides of a 9-inch pie plate. For a firmer crust, bake at 350°F (175°C) for 8–10 minutes and let it cool completely. Skip the baking if you prefer a softer crust.

Make the Pineapple Coconut Filling: Drain the crushed pineapple in a fine-mesh sieve for 10–15 minutes, but don’t squeeze out all the juice. In a large bowl, beat softened cream cheese until smooth. Gradually add the sweetened condensed milk and mix until well combined. Stir in vanilla extract and the drained pineapple. Fold in ¼ cup shredded coconut.

Assemble the Pie: Pour the pineapple filling into the cooled graham cracker crust and spread it evenly. Cover with plastic wrap and refrigerate for at least 4 hours, or preferably overnight.

Make the Coconut Whipped Cream: Chill the mixing bowl and whisk in the refrigerator for 10 minutes. Beat cold heavy cream in the chilled bowl on medium speed until soft peaks form. Gradually add powdered sugar and coconut extract, continuing to beat until stiff peaks form.

Finish the Pie: Once the filling has set, remove the pie from the refrigerator and spread the whipped cream evenly over the top. Garnish with toasted shredded coconut and pineapple wedges if desired. Chill for another 30 minutes before slicing and serving.