In a stand mixer or in a large bowl, mix granulated sugar, cocoa powder, olive oil and vanilla extract together. Slowly add one egg at a time. Set aside.
In a medium bowl whisk together the flour, baking powder, salt.
Add the dry mix to the wet mix in the stand mixer or into the large bowl of wet ingredients. Combine, but try not to over mix. Dough should be thick and keep shape.
Place dough into the smaller bowl if you need for room. Cover with plastic wrap and stick into the freezer for about 45 minute (make sure you set a timer). Or you can refrigerate for 2 hours. Add the powdered sugar to a bowl and set aside until cookie dough has chilled.
You may need two cookie sheets or you will need to bake two batches. On a parchment lined cookie sheets, use a small cookie scoop and gently roll the chocolate brownie crinkle dough into 1 inch balls, one at a time. Dip them well in the powdered sugar and place on the cookie sheet about one inch apart.
Bake on 350º for about 10 minutes. Let the cookies cool for about 5 minutes on cookie sheets once done. Unwrap the candy cane kisses and gently press them into the center of the brownie crinkle cookie. If the cookie splits a little while pressing the kiss into it, simply gently press it back together and hold together for a little while it should keep its form.