In a large bowl, combine butter, sugar, salt, and vanilla. Mix together until incorporated. It doesn't need to be fluffy - just until it's relatively smooth. It's super easy to do this by hand, but you can also use an electric mixer fitted with the paddle attachment!
Add your flour to the butter mix, and stir together until a dough forms. The dough should be soft but it shouldn't stick to your fingers. If it does, mix in an additional tablespoon of flour at a time until it reaches the right consistency.
Portion out about 3 tablespoons of dough into a separate bowl, and add in cocoa powder. Mix together until combined.
Working with the remaining dough, add food coloring until you reach your desired shade of orange. ** (see notes) If the food coloring has softened the dough too much (to the point where it sticks to your fingers if you press it), gradually add more flour until it stops sticking.
Cover both portions of dough with plastic wrap, and set aside in the fridge for 1 to 2 hours, or until firmed.
Preheat your oven to 350°F. Line a large baking sheet with parchment paper and set aside.
To shape the mini pumpkins, take a portion of the orange colored dough (about 2 tablespoons large), and roll into a tall oval. Place the orange dough onto your parchment lined baking sheet.
Using a skewer, toothpick, or similarly shaped utensil, press vertical indents into the side of the orange dough to create the lines you see on real pumpkins (see above post for visual). Take a very small piece of the brown cookie dough, and roll into the shape of a stem. Place the stem on top of the orange dough.
Repeat the shaping process with the remaining dough, leaving about 1 inch of space between each cookie on your baking sheet. Place the cookies in the freezer for 10 minutes to allow the cookies to firm up.
Bake the semi-frozen cookies in the center of your preheated 350°F for 15 to 20 minutes, or until golden brown along the sides and bottom. The cookies will spread and flatten slightly.
Cool the cookies completely on your baking sheet before serving!