Preheat oven to 350 F & line baking sheet with parchment paper.
Microwave butter until soft but not melted entirely in large mixing bowl.
Add flour, baking powder, sugar, egg, & vanilla to the butter. Knead mixture with your hands while gradually adding in ¼ cup of milk as needed to help combine mixture.
Scoop cookies onto parchment paper using a cookie scooper & place them about 3 inches apart. (You can make cookies in batches if they do not all fit on your tray)
Place tray in freezer for 15 minutes. Remove & flatten cookie dough in palm of your hand. Add one unwrapped Hershey's Candy Cane Kiss to the center of your cookie. Wrap the dough around the kiss & roll into a ball. Place back onto tray 3 inches from other cookies & repeat until tray is full.
Bake cookies for 12-15 minutes. Take remaining unwrapped Kisses & place in microwavable bowl for 30 seconds. Stir until smooth & drizzle over cookies.
Serve warm & enjoy!