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Toast the Pecans: Place the pecans in a large, dry skillet over medium-high heat. Toast for 3-5 minutes, stirring frequently, until they become fragrant. Be careful not to burn them. Remove from heat and set aside.
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Prepare Baking Sheets: Line two large baking sheets with parchment paper and lightly coat with non-stick cooking spray. Arrange the toasted pecans in groups of three, leaving about an inch of space between each cluster.
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Make the Caramel: In a medium saucepan, melt the butter over medium-high heat. Stir in the brown sugar, corn syrup, and sweetened condensed milk. Cook and stir continuously until the mixture reaches 235-240°F (soft-ball stage) on a candy thermometer. This will take about 10-15 minutes.
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Finish the Caramel: Once the caramel reaches temperature, immediately remove the saucepan from the heat. Stir in the vanilla extract.
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Assemble the Clusters: Carefully drizzle about ½ tablespoon of the hot caramel over each pecan cluster, using a spoon to help the caramel pool over the nuts. Set the trays aside.
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Melt the Chocolate: Create a double boiler by filling a pot with about 1-2 inches of water and placing a heatproof bowl on top, ensuring the bottom of the bowl does not touch the water. Bring the water to a gentle simmer over medium heat. Add the chocolate chips to the bowl and stir until completely melted and smooth. Remove the bowl from the heat and stir in the shortening until fully incorporated.
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Top with Chocolate: Spoon about ½ tablespoon of the melted chocolate over the center of each caramel-coated cluster.
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Set and Serve: Allow the clusters to cool completely at room temperature until the chocolate is firm. Once set, serve immediately or store in an airtight container with parchment paper between layers.