Wash the apples well and cut them into thick rounds, about half an inch wide. Thicker slices hold the sticks better and feel sturdier in your hand. I remove the seeds with a small knife so every bite stays smooth.
Pat both sides of each slice with paper towels until no moisture is left. This step matters more than anything else in the recipe. Wet apples make the caramel slide right off.
Take one caramel wrap and press it around the edge of an apple slice. Smooth it with your fingers so it hugs the fruit. As the apple sits, it releases a little juice, so I work quickly and keep my towel close.
Gently press a lollipop stick into the top of each slice. Push it in about halfway so it feels secure. Then set the pop on a parchment-lined baking sheet and repeat with the rest.
Place the vanilla candy melts in a microwave-safe bowl. Heat them in short bursts of 30 seconds, stirring each time, until smooth. Spoon the melted candy into a small piping bag and snip a tiny corner.
Pipe two triangle eyes, a small nose, and a wide, toothy smile onto each apple slice. Work slowly, and make each face a little different. Silly faces are my favorite, and they always get giggles.
While the candy is still wet, sprinkle black sugar over the faces. The sprinkles stick right away and make each jack o lantern look bold. Tap off the extra gently so the lines stay sharp.
Leave the pops on the tray for about 15 minutes until the candy firms up. You can slide them into the fridge to speed this up. Serve them as soon as the faces feel set