Preheat the oven to 350 F. Line 2 baking sheets with parchment paper and set aside.
In a medium bowl, whisk together the flour, baking powder, espresso powder, and salt. Set aside.
Melt the butter in medium saucepan over medium heat or in microwave-safe bowl in 20 second increments.
Whisk in the cocoa powder and brown sugar. Whisk in the eggs thoroughly, one at a time.
Add the wet ingredients into the dry ingredients and mix until just combined. Scoop out 2 tablespoons of cookie dough rounds and use your hands to roll into a ball, then flatten to 1/4 inch (6mm) thick. Add a Rolo candy to the center and wrap the dough up around the candy. Roll this into an even ball, then roll it into the confectioner sugar until heavily coated. Repeat with remaining dough and candy.
Place the cookies 2 inches apart on the prepared baking sheets. Bake in preheated oven for 8 to 10 minutes, until the cookies look crinkly and spread slightly.
Allow the cookies to sit on the baking sheet for 5 minutes before transferring to a wire rack to cool briefly. Make sure to serve warm to get the gooey caramel.