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Chocolate Caramel Shortbread Cookies

makes about 40 candies

24 individually-wrapped caramels, unwrapped
1 can sweetened condensed milk (not evaporated milk)
1/2 stick of butter
1 10-oz. package of Lorna Doon shortbread cookies
4 cups (2 12-oz packages) semi-sweet chocolate chips
1/3 cup shortening
1 tsp. glycerin

1. In a medium microwave-safe bowl, combine caramels, sweetened condensed milk, and butter. Microwave 1 minute, stir, and continue microwaving in 1-minute intervals until caramels are about half-melted (this will take from 2 - 4 minutes all told). Continue to stir until caramels have melted completely. Cool somewhat to thicken.
2. Line 2 cookie sheets with waxed paper. Set aside. Using a soft, clean pastry or basting brush, brush excess crumbs from each cookie. This may seem anal, but it takes just a few minutes and makes the caramel-spreading and chocolate-dipping much cleaner. Plus it gives your caramel a chance to cool a bit.
3. Using a butter knife or frosting spreader, spread the top of each cookie with caramel and place on cookie sheet. Freeze for 30 minutes or so.
4. Melt chocolate, shortening, and glycerin in a double boiler over very low heat. Remove from heat.
5. Leave second tray of cookies in the freezer while you dip the first. Using scissor-style kitchen tongs, pick up cookie so that opposite corners slip into the sides of the tongs (see picture below). This will hold it securely while you dip it without disturbing the finish of the candy. Dip the cookie into the chocolate and swirl a couple of times to coat. Tap tongs along side of boiler to shake off excess chocolate. Drop on waxed paper to cool. Repeat with remaining cookies.
6. Work quickly so that the caramel stays cold and neat. When you get to the bottom of the chocolate, you'll need to swirl a few times in one direction, then switch directions to coat completely. You'll want to heat the chocolate a bit between trays, as the cold caramel will have caused it to thicken a bit.
7. Allow candy to cool and harden for several hours before storing in an airtight container. Separate layers with waxed paper, if you like, to keep neat. Use any extra caramel and chocolate to make Turtle Clusters.

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