Place your softened butter in a bowl or stand mixer. Cream the butter using the stand mixer with a whisk attachment or hand mixer until smooth and fluffy, about 5-7 minutes. Scrape down the sides as needed.
Add the apple sauce and vanilla to the butter and beat together until combined.
Whisk and sift together the flour, sugar, and chocolate chips. Add it to the butter 2 tbsp to ¼ cup at a time, beating it with the stand mixer or hand mixer until fully incorporated before adding more. Scrape down the sides as needed.
Once you near the end of the flour/sugar mixture (about ¼ to ½ cup left), add just a bit at a time and mix by hand until a dough forms that stays together without sticking to your hands.
Split the dough in half. Place a sheet of parchment paper on a surface and lightly flour. Place one half of the dough ball on it and lightly flour the top of it. Place another sheet of parchment paper on top and then roll out the dough until it is a ¼ inch thick with a rolling pin. Repeat with the second half of the dough.
Place the rolled out dough in the fridge for 20 minutes.
Preheat the oven to 350°F. Line a baking tray with a sheet of parchment paper.
After the dough has stiffened a bit, remove it from the fridge and cut circles using a 2 inch across cookie cutter. Place the circles on the baking tray.
Reroll the extra pieces of dough and repeat.
Once all of your circles have been cut, place ½ of a peanut butter cup into the center of each circle.
Fold up three sides of each circle and pinch the sides the touch together to create the triangle shape. Be sure to seal/pinch the edges well so that they don't fall apart or leak when baking.
Place the baking tray in the freezer for 20 minutes.
Remove from the freezer and transfer the baking tray to the oven. Bake for 20 minutes, or until the bottom edges of the cookies start looking golden brown.
Remove and immediately transfer to a wire rack to cool completely.