Preheat oven to 350°.
Add granulated 1 1/2 cups granulated sugar to a bowl. Zest 2 oranges into the sugar and mix together with your fingers until well combined. Set aside.
In a mixing bowl, add 1 cup granulated sugar, powdered sugar, softened butter and vegetable oil and mix on medium speed until fluffy, about 2 minutes.
Add eggs, orange extract and vanilla extract, mix until combined.
Next, add flour, baking soda, cream of tartar and salt. Mix on low speed until flour is just combined. Raise to medium speed and beat about 1 minute.
Add 1 cup of cranberries and mix until combined.
Using a small cookie scoop, scoop dough into balls.
Roll in orange sugar mixture and place on a lined or greased cookie sheet.
Smash the cookies with the bottom of a glass.
Chop remaining cranberries and add a few cranberry pieces to each cookie. This is optional, all cranberries can be added into the cookie dough if preferred.
Bake for 12- 14 minutes until lightly browned around the edges.
Cool on cookie sheet 2 minutes. Move to a wire rack to cool completely.