Rolling pin, baking trays, parchment paper, decorating scribe
Roll out your dough and cut all the pumpkin shapes first!
Transfer your pumpkins to a baking sheet and chill in the freezer for 5-10 minutes
For ease of use when applying the face, dip it in flour so it's nice and dusty (or icing sugar if you really want to avoid excess flour; personally I find flour more effective though.)
For stamp application, gently press the face into your pumpkin shape on the baking tray.
Fort applying the face as a cut-out, ensure your raw cookie is chilled, and the face cutter is coated in flour (flour is your best friend here! The dough will get trapped in the facial features SUPER easily. It's best if your dough is chilled, rolled, cut, and floured before attempting to punch out the face.)
If the pieces stick to the pan, use your cookie scribe too remove the pieces. If you can't pull the cutter away, and the dough is stuck in the small facial features, use the blunt end of a small spoon or similar to pop the dough out of the cutter from above. Patience is key here, and also lots of flour!
You can also use a pen blade or small knife to smooth out the edges of your jack-o-lantern if small pieces remain in the facial features.