12 ounces Semisweet Chocolate Chips, or milk chocolate chips
Preheat oven to 375°F. In a standing mixer fitted with the flat beater, or in a large bowl with a hand mixer, blend together the butter and confectioner’s sugar. Mix in the vanilla extract and egg until well blended. In a separate bowl, briefly whisk together the flour and salt, and gradually add to the butter and sugar mixture. When a dough forms, cover the bowl and refrigerate for two hours.
When the dough is chilled, roll out on a floured surface to 3/8-inch thickness. Cut out your circles and place on parchment paper-lined baking trays. Insert sticks, making sure none of the sticks touch the other cookies. Bake until the edges are golden, about 15 minutes. Let cool completely.
Unwrap and place the caramels in a microwave-safe bowl. Add the half and half. Microwave caramels for 90 seconds. Stir well to completely melt the caramels with the residual heat. If needed, heat in the microwave for additional 15-second intervals.
Spread the melted caramel on each cookie and let set 10 to 15 minutes.
In a microwave-safe bowl, place the chocolate chips. Melt the chocolate at 70 percent power for 90 seconds. Stir well to completely melt the chocolate with the residual heat. If needed, heat for additional 15-second intervals.
When cool enough to handle, transfer the chocolate to a decorating bag (if using). Snip the tip and pipe circles of chocolate on each cookie. You may also spread the chocolate with a knife. Refrigerate until the chocolate is fully set, about half an hour.
You’ll also need the following supplies: 1 ½-inch circle cookie cutter, 6-inch lollipop sticks, and an optional decorating bag.