Prepare the caramel, which can be done days before baking day. Add the sugar to a large non-stick sauce pan over medium heat. Use a rubber spatula to toss around the sugar until it melts. The sugar will turn beige and clump up at first, but then it will start to melt.
Once it’s totally liquified, cut your butter into ten chunks. Using a whisk, add the butter chunks to the sugar and vigorously whisk- the mixture will bubble and sizzle. Keep whisking for a couple minutes until the butter no longer separates to the outer edges of the pan. It might take longer depending on your pan and heat- just be patient!
Next, pour in the heavy cream and vigorously whisk again. Let it bubble for another two minutes, stirring occasionally, until the mixture turns a deep amber brown color.
Remove the caramel from heat and whisk in the vanilla extract and salt. Let the caramel cool for at least 20 minutes before using. You can also store this in an airtight container in the refrigerator for up to one month.
Now the hard part is over! Onto the brownies. Preheat the oven to 350 degrees and line a 9×9-inch baking pan with parchment paper.
In a medium bowl, whisk together the flour, cocoa powder, salt, and confectioners sugar.
In a small microwave-safe bowl, heat the butter and chocolate chips in 30-second increments until the mixture is melted and smooth.
In a large bowl, whisk up the eggs, sugar, and vanilla extract. Pour the melted butter/chocolate into those wet ingredients and whisk to combine well.
Use a spatula to fold the flour mixture into the wet ingredients until just combined. No need to over-mix, but you want to get any big clumps out.
Next, prepare the pumpkin filling. In a medium bowl, beat all of the filling ingredients on high speed for a couple minutes until smooth and creamy.
Now, it’s time to layer in the pan! Add half of the brownie mixture to the pan first. This part can get tricky- it will seem like there’s not enough brownie batter, but there is! Use a spatula and the tips of your fingers to gently spread the batter to every edge and corner. Spread the pumpkin filling on top of that layer and smooth it over with a spatula. Take heaping spoonfuls of your caramel and disperse the caramel as evenly as possible on top of the pumpkin filling. Finish with the second half of the brownie batter, using a spatula and your fingers to spread it and smooth it as much as possible.
Bake the brownies for 32 to 35 minutes. When a toothpick comes out of the center clean, they’re done!
Let them cool completely in the pan before serving. Ideally, if you have time, transfer them to the refrigerator once they’ve cooled and let them chill for at least an hour or overnight before cutting. They can get messy trying to cut them at room temperature! These babies can be enjoyed for up to five days stored in the refrigerator, or frozen for up to two months.
