Preheat your oven to 350 degrees Fahrenheit.
In a large mixing bowl, mix your flour, cocoa powder, and Chocolate Fudge pudding mix together. When measuring the flour, make sure to scoop up the flour with a spoon and add it to your measuring cup, one spoonful at a time. This helps obtain the correct amount of flour without needing to weigh it. Once you have a cup, level it out by running a knife across the top of the measuring cup.
In your electric mixer, combine the white and brown sugars with the butter using the paddle attachment until they are creamed together.
Add in your egg, 1 tablespoon canola oil, and vanilla extract and mix to combine.
Slowly add in the flour, cocoa powder, and pudding mixture to the wet ingredients and combine. The combined mixture will be crumbly but still form a ball if picked up and molded into a ball. If it is too crumbly, add in another tablespoon of canola oil.
On a floured surface, roll out the dough to about a 1/4 of an inch thick & cut out your cookies. A great tip is to flour your rolling pin and any cookie cutters you may be using. Transfer the cut out cookies to a baking sheet lined with a silicone mat or parchment paper. Bake for 9-10 minutes and let cool on the baking sheet. The dough will be done when the center of the dough doesn’t look wet. It is better to undercook the cookies than to overcook them, as it will be difficult to watch for burns with these dark sugar cookies.
Optional but highly suggested: Place the cooled cookies into an airtight container and freeze them overnight. Remove the container from the freezer 1 hour before decorating for soft brownie chocolate cut out cookies.