Prep the pineapple: Open the can and drain crushed pineapple in a fine-mesh sieve, pressing gently with a spoon to remove excess liquid.
Reserve a few tablespoons of the juice.
Make the cream base: In a large bowl, beat the softened cream cheese, sugar, vanilla, and a pinch of salt until smooth and fluffy. Scrape down the sides as needed so there are no lumps.
Mix the pudding: In a separate bowl, whisk instant pudding mix with cold milk and 2 tablespoons reserved pineapple juice until thickened, about 1 to 2 minutes.
Combine: Add the pudding mixture to the cream cheese mixture and beat until well combined and silky.
Fold in the pineapple: Gently fold in the drained crushed pineapple. Avoid overmixing; you want some texture throughout.
Fold in the whipped topping: Use a spatula to fold in the whipped topping just until the mixture is smooth and airy.
Fill the crust: Spoon the filling into the graham cracker crust, smoothing the top with the back of a spoon or an offset spatula.
Chill to set: Cover and refrigerate for at least 4 hours, or overnight for the cleanest slices.
Garnish and serve: Before serving, top with toasted coconut, a few pineapple bits, and a pop of lime zest if you like.
Slice with a clean, sharp knife.