Preheat your oven to 375 ℉ so it is ready for baking. Unwrap all 48 Hershey's Kisses and set them aside. Line a baking sheet with parchment or have an ungreased cookie sheet ready.

In a large bowl, beat together the creamy peanut butter and shortening until well combined and smooth.

Add in both the packed brown sugar and the regular sugar and beat until fully incorporated. Next, add the egg (room temperature), milk, and vanilla. Beat everything together until the mixture is light and fluffy. I find letting the egg come to room temperature makes the dough mix more evenly.

In a separate bowl, sift together the wheat flour, baking soda, and salt. Gradually add the dry ingredients into the peanut butter mixture, mixing just until incorporated. Don't overmix for the best cookie texture.

Shape the dough into one-inch balls, using about a tablespoon of dough for each. Roll each ball in your choice of red or green sugar for a festive appearance. Place the coated dough balls onto the prepared, ungreased cookie sheet, spacing them evenly.

Bake the cookies for 8–10 minutes or until they are lightly browned. Immediately after removing the cookies from the oven, gently press a Hershey's Kiss into the center of each cookie. I love this part—the chocolate gets just soft enough to melt in your mouth!

Allow the cookies to cool on the baking sheet for a few minutes before transferring them to a wire rack to cool completely. Once cooled, the cookies are ready to serve or store.