Prepare the pudding: whisk the vanilla pudding mix into 2 cups of cold milk in a mixing bowl until smooth and slightly thickened, then refrigerate for about 10 minutes to set.
Meanwhile, make the cookie crumble: combine flour, cocoa powder, sugar, and melted butter in a bowl, then mix until crumbly and evenly coated.
Spread the cookie crumble onto a baking sheet and bake in a preheated oven at 350°F (175°C) for about 8-10 minutes until fragrant, then let cool.
Once cooled, crumble the baked cookies into small pieces and set aside.
Layer the pudding into individual cups or containers, filling them about halfway.
Sprinkle a generous layer of cookie crumble over the pudding layer for added texture and flavor.
Add another layer of pudding on top of the cookie crumble, then repeat the crumble layer if desired for a tall, spooky effect.
Place a chocolate tombstone or candy gravestone on each cup to resemble a graveyard, pressing gently to set in place.
Finish by adding more cookie crumble around the bases of the tombstones to blend them into the scene.
Chill the completed pudding cups in the refrigerator for at least 1 hour before serving to let flavors meld.
Serve the spooky graveyard pudding cups chilled, with extra decorations if desired for more haunting effect.
