Preheat the oven to 350 degrees.
Using a hand mixer, beat together the cake mix, softened butter, and egg until incorporated and crumbly.
With your hands, press the crumbs together to make a stiff dough.
Roll a rounded tablespoon of dough into a ball. It should be just under 1.5 inches in diameter. Place on lined cookie sheet.
Use a cup or glass with a flat bottom to gently flatten the dough balls until they are 2 inches in diameter.
Bake cookies 11-12 minutes until set. Edges will not be brown.
Allow cookies to cool before topping.
Place caramel bits and milk in a microwave safe bowl. Microwave in 30 second intervals, stirring well between each interval, until melted and runny.
Scoop a little more than a teaspoon of caramel onto each cookie. After every 6 cookies, stop and use a butter knife or offset spatula to spread caramel near the edges fo the cookie.
Melt the milk chocolate chips in 30 second intervals, stirring well between each interval. Stir in the vegetable oil or shortening.
Scoop a generous teaspoon of chocolate onto each cookie, and spread using a knife or offset spatula.
Allow cookies to cool before serving. You can put them in the fridge to cool; however if you leave them in the fridge too long the chocolate may get streaky or spotty.