Cookies-

In the bowl of a stand mixer fitted with a paddle attachment or in a large bowl using a hand mixer, combine the butter, sugar, and powdered sugar till light and fluffy. Add the oil, eggs, and vanilla and mix till well combined again.

In a medium bowl combine the flour, sifted cocoa powder, baking soda, baking powder, salt, cream of tartar, and crushed candy canes. Mix together till well combined.

Add the flour mixture to the butter mixture all at once and mix, scraping the sides as needed, till combined. Don’t over mix. You want your dough to be soft, but also not overly sticky.

Put the ½ cup sugar in a small bowl. With a flat-bottomed glass or cup, press the bottom into the bowl of cookie dough to get the bottom to be a bit greasy (this way it will pick up the sugar from the bowl, you only need to do this the first time). Dip the glass into the sugar and press a cookie ball till it’s about 1/2 inch thick. If you want them a bit thinner then press a bit more and bake a bit less. Dip the glass in between pressing each cookie.

Place in oven and bake for about 7-9 minutes. You want to slightly under-bake these cookies or they will be dry instead of soft and moist. Pull out of the oven when the middle still looks unset. Let the cookies cool for about 3-4 minutes on the baking sheet before moving to a cooling rack.

Frosting-

In the bowl of a stand mixer fitted with a whisk attachment or in a large bowl using a hand mixer, combine the butter and sifted powdered sugar till light and creamy. Add the vanilla, peppermint extract, and heavy cream and mix/whip for at least 3-4 minutes. If your frosting is too soft you can either refrigerate it for 10-15 minutes before frosting your cooled cookies, or add a bit more powdered sugar.

Frost the cookies and dust with crushed candy canes, if desired.