Preheat the oven to 350 degrees F and line two baking sheets with parchment paper.
In a large bowl, mix together the chocolate cake mix, canola oil, and eggs until well combined.
Use a medium cookie scoop to place scoops of the cookie dough on the baking sheets, leaving at least two inches of space between them.
Bake for 9-12 minutes or until the edges of the cookies are set.
Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack to finish cooling.
For the Frosting
In a large bowl, beat the room-temperature butter until it becomes light and fluffy.
Scrape down the sides of the bowl, then add powdered sugar, vanilla extract, and a pinch of salt. Beat until well combined.
Gradually add milk (1/2 tablespoon at a time) until you achieve the desired frosting consistency. It should be easy to spread onto the cookies but firm enough not to slide off.
Assembly
Frost each cookie generously with the prepared frosting.
Place the white sanding sugar on a small plate and gently press the frosted side of the cookie into it to create an even coating.
Apply a small amount of frosting to the bottom of a peppermint pattie and attach it to the lower third of the cookie to create the pad of the bear's foot.
Gently press four brown M&Ms above the peppermint pattie to create the bear's toes.
Allow the frosting to set for 15-30 minutes before serving.
Notes
Store these cookies in an airtight container at room temperature for 2-3 days or in the refrigerator for up to five days. Keep in mind that storing them in the fridge may affect the appearance of the M&M toes.
Let the frosting set completely before stacking the cookies. Consider placing parchment or wax paper between layers if you need to stack them.
You can use sweetened shredded coconut instead of white sanding sugar for the fur.
If you prefer, you can use brown Reese's Pieces or Junior Mints for the toes, but note that their sizes differ from M&Ms, affecting the look of the cookies.