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. Add in the egg and vanilla extract. Beat until smooth and creamy.
Add the dry pudding mix and brownie mix. Beat to combine. (The dough will be thick and takes a while to form into dough. This is intended. Just keep mixing and it will all come together)
Stir in the chocolate chips. 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). Roll it into a ball. Shape dough balls into wide, thick discs about 2 inches wide and 1/2-inch thick. Place 6–8 cookies on the prepared cookie sheet, giving cookies ample room.
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 and let cool for 5 minutes on sheet pan before gently transferring to a cooling rack to finish cooling.
Filling
In a large bowl, using electric hand mixers, mix peanut butter, softened butter, powdered sugar, salt, and vanilla until smooth. Roll the mixture into equal sized balls, making as many balls as you have baked cookies. Place one ball on each completely cooled cookie. Gently press to flatten the filling onto the cookie. Smooth the top with your finger so chocolate goes on nicely.
Chocolate Topping
In a microwave safe bowl, heat the chocolate chips and coconut oil in 20 second bursts, stirring between each for 20 full seconds, until melted and smooth. Carefully dip each cookie into the chocolate, lifting gently and tapping to spread it out. If the peanut butter topping starts to slip off, use a spoon to lightly pour the melted chocolate over the top instead. Aim to just cover the peanut butter filling so a little of the filling still shows.
Video
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.Storage: Store plain baked cookies at room temperature for up to 3 days. Freeze unbaked dough up to 3 months; bake from frozen. Assembled cookies (with peanut butter and chocolate) are best within 2 days and don’t freeze well.