First, add the butter and sugar to a bowl and cream together until smooth and creamy.
Next, add in the egg yolk and clear vanilla extract and mix well, again until smooth.
Next, add in the flour, remaining dry ingredients, and mix until the dough comes together.
Divide your dough into about ⅔ and ⅓. The ⅓ portion of the dough will be the dough you dye. Dye the ⅓ portion of the dough orange, and set the ⅔ portion of plain dough to the side, or place in the refrigerator.
Roll the dyed dough into an even disk that is about an inch thick (thicker is better so that the dough is easier to work with), ensuring an even surface so that the individual pumpkin shapes stick together smoothly and evenly. Place in the freezer for about 20 minutes until the dough is firm, but not frozen.
Remove from the freezer and using a small pumpkin cookie cutter, cut out the small pumpkin shapes until all the dough has been used. Stack the pumpkin shaped dough together, gently squeezing them and shaping them together to create a cohesive log. You want to try to eliminate any space between each pumpkin as this will lead to uneven baking and gaps in the dough.
Place the pumpkin shaped log in the freezer until firm. This is an important step as you don't want the pumpkin dough to lose its shape while placing the plain dough around it.
Once firm, using your pliable plain dough, wrap the plain dough around the pumpkin shaped dough log, filling in the gaps as tightly as possible around the stem, and surrounding the pumpkin dough as evenly as possible. Roll gently until the dough creates a long round tube.
Place in the freezer until very firm, and preheat the oven to 350.
When the dough is firm, slice the cookies into 1 inch cookies and place in the oven to bake for 11-12 minutes. These are best just slightly golden and underbaked so they are soft and chewy.