In a large bowl, add the flour, baking soda, cornstarch, and salt. Mix to combine.
Microwave the butter until softened, but not fully melted.
To the same bowl (as the dry ingredients), add in the sugars, butter, eggs, and extract. Mix well with clean hands to combine.
Fold in the candy corn, and chocolate chips.
Cover dough to make it airtight and refrigerate to chill for a minimum of 30 minutes. However, any longer (up to 3 days is better).
Once dough is chilled, preheat oven to 325 degrees fahrenheit.
Line your baking sheet with parchment paper. If you are using a standard size sheet, bake only 6 cookies per batch (makes 2 batches).
Form dough into 12 larger balls and 12 smaller balls.
Make sure there are no candy corns popping through the "bottom" of the cookie dough.
Place unwrapped Rolo in the center of the cookie, but do not let it show in the bottom of the cookie.
Cover Rolo space with the smaller cookie ball, and pat into one jumbo cookie ball.
Space cookies out 6 per standard size baking sheet.
Bake for 14-15 minutes at 325 degrees fahrenheit.
Remove cookie sheet from oven, and allow cookies to stay on the baking sheet for at least 5 minutes to firm up. Cookies may be a little sticky from melted candy corn, but gently transfer them to a cooling rack and repeat the baking process with the next 6 cookies.
Allow all cookies to fully cool before storing or eating. Cookies keep for up to 1 week in an airtight container.