• Preheat oven to 350 degrees. Line 2 8x8 inch pans with foil or spray with non-stick cooking spray. Set aside.
• In a large bowl, combine sugar, butter, milk, eggs and vanilla extract until smooth.
• In a separate bowl, sift together flour, cocoa powder, baking powder and salt.
• Slowly add dry mixture to wet mixture, mixing until just combined. The batter will be stiff and sticky.
• Divide batter evenly between two prepared pans, smoothing the top with an offset spatula. Bake for 18-22 minutes or until a toothpick inserted in the center comes out clean. Try not to overbake.
• Remove from oven and cool brownies for about 15-20 minutes in the pan before removing. Cool completely before proceeding to next step.

For Coating:

• {I'd hate to sound Ina here, but it's true that the good stuff is the easiest to work with. I used 1 ½ bars of 70% cocoa Lindt chocolate. It melts like a dream and is easy to pour. You can use whatever chocolate you'd like, but good chocolate makes life easier.}
• Break chocolate into pieces and microwave at 30 second intervals, stirring until completely melted.

For assembly:

• - Place one layer of brownies {smoother side down} back in a foil-lined pan {flaps hanging over make for easy removal}. Pour about a cup or more of pumpkin caramel directly over brownie. Smooth out into an even layer with an offset spatula and makes sure it gets all the way to the edges, they'll be trimmed so it's ok if it's messy.
• - Carefully place the second layer of brownies {smoother side up} over top of the caramel layer. Push down lightly to affix to caramel. Your caramel will most likely still be warm and will need to set. The fastest way to do this is to refrigerate for a little while - 30 minutes to an hour should do.
• - Once the caramel is set, remove the whole brownie from the pan carefully. Using a sharp knife, cut the very edges off to make clean sides. Cut the brownie into 9 equal pieces. Insert a popsicle stick into each brownie and place onto a cooling rack.
• - Pour about a tablespoon of melted chocolate over each brownie pop to coat, allowing to drip over sides. Refrigerate to set for about 10-15 minutes. Remove from fridge, flip, and coat the other side. Refrigerate until chocolate is set.
• - Drizzle the tops with melted caramel and immediately sprinkle with flaked sea salt if desired. Allow caramel to set.