Preheat oven to 350°F. Line a large sheet pan with a silicone liner and set aside. Bring the cream cheese and butter to room temperature by either leaving out for 1 hour or by microwaving (unwrapped) cream cheese in increments of 5–10 seconds until soft. Separately microwave the butter for 5 seconds, flipping to the other side, and microwaving another 5 seconds. Be careful not to melt or overly soften either ingredient.
In a large bowl fitted to a stand mixer (or use a hand mixer), cream together the cream cheese and butter until completely smooth. Beat in the egg and vanilla extract. Beat until smooth and creamy.
Add the dry pudding mix and brownie mix(see note 1). Beat to combine. (The dough will be extremely thick and takes a while to form into dough. This is intended. Just keep mixing and it will all come together, even though it seems like it won’t.)
Stir in the mint baking chips and milk chocolate chips (see note 2).Cover the dough tightly and refrigerate for 20–30 minutes.
Measure each dough ball to be a full, packed 2 tablespoons of dough (40 grams). Knead the dough ball to get the chocolate chips to stick into the dough, then roll it into a ball. Shape dough balls into wide, thick discs about 2 inches wide and 1/2-inch thick. You should get about 28–30 cookies from this batter. Place 6–8 cookies on the prepared cookie sheet, giving cookies ample room to spread.
Bake each batch for 10–14 minutes. Slightly underbaking these cookies gives them a chewy taste and texture like ultra fudge-y brownies, so err on the side of slightly under-baking. Remove from oven (see note 3).
Frosting
While the cookies are cooling, prepare the frosting. Beat together softened to room temperature cream cheese and butter until completely smooth. Add peppermint extract and optional green food coloring. Add the powdered sugar. Beat until smooth and combined (it may seem like it’s not coming together, but resist the urge to add any liquid; it is intended to be a thick frosting). Frost each cooled cookie. If needed, gently press the frosting down to adhere to the cookie.
Chocolate Topping
In a microwave safe bowl, heat the chocolate chips and coconut oil in 20 second bursts, stirring between each, until melted and smooth. Dip each cookie into the chocolate, lifting gently and tapping to spread it out. If the frosting starts to slip off, use a spoon to lightly pour the melted chocolate over the top instead. Aim to just cover the frosting so a little of the green still shows.
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Notes
Note 1: It is very important you get the right-sized brownie mix (18 ounces). Otherwise, these cookies won’t turn out right! I tested many brownie mixes, and the one called for in the recipe was by far my favorite.Note 2: Unwrap and coarsely chop Andes Mints if you aren’t able to find mint baking chips.Note 3: Sometimes the edges of freshly baked cookies have a tendency to leak out. Right out of the oven, use the back of a spoon or metal spatula to press the edges in toward the center of the cookie.Storage: Store leftover cookies in an airtight container at room temperature for up to 3 days. If frosted, keep them in the fridge for up to 5 days.