• Start by letting the butter truly soften at room temperature for about an hour – you should be able to easily press your finger into it but it shouldn’t be melty. This will help everything mix evenly.
• Cream the softened butter and brown sugar in a large bowl until it’s really light and fluffy, about 3-4 minutes. You’ll see the color change to a lighter brown and the texture will become almost whipped. Don’t rush this step – it’s key for tender cookies.
• Beat in the egg and vanilla until the mixture looks smooth and well-combined, about 30 seconds.
• In a separate bowl, whisk together the flour, cocoa powder, and salt. The cocoa tends to be lumpy, so break up any clumps with your whisk.
• Gradually mix the dry ingredients into the butter mixture, about 1/2 cup at a time. The dough will get pretty thick – that’s exactly what you want. Keep mixing until you don’t see any dry cocoa streaks.
• Cover the dough and chill it for at least 1 hour. This prevents the cookies from spreading too much and makes the dough easier to handle.
• When you’re ready to bake, preheat your oven to 350°F and line your baking sheets with parchment paper.
• Roll the dough into 1-inch balls (about the size of a walnut). Place them 2 inches apart on the baking sheets – they’ll spread a bit.
• Bake for 10-12 minutes. The cookies are done when the edges are set but the centers still look slightly soft – they’ll continue cooking a bit on the hot baking sheet. You won’t see them brown like regular cookies because of the cocoa.
• While still warm, make a small indent in the center of each cookie with the back of a teaspoon. Let them cool completely on the baking sheets.

For the caramel filling:

• Unwrap the caramels and place them in a microwave-safe bowl with the heavy cream. Microwave in 30-second intervals, stirring between each, until smooth and completely melted. Watch carefully – caramel can bubble over quickly.
• Spoon about a teaspoon of warm caramel into each cookie indent. Place a pecan half on top of the caramel while it’s still warm. Let these set for about 30 minutes.
• For the final touch, melt the chocolate chips with the shortening in the microwave in 30-second intervals, stirring between each, until smooth. The shortening helps make the chocolate more fluid and gives it a nice shine.
• Using a spoon, drizzle the melted chocolate over the cookies in a zigzag pattern. Let the chocolate set completely before storing, about 1 hour at room temperature.