Preheat the oven to 350°F. Line a half sheet pan with parchment paper.
To make the brownies: Add the olive oil, cane sugar, cocoa powder and boiling water to a large mixing bowl. Mix with a hand mixer until smooth.
Add the melted chocolate and milk and mix to combine.
Add in the all purpose flour, salt, and vanilla bean and mix until a smooth brownie batter forms.
Transfer to the half sheet pan and spread it out evenly.
Bake for 25 to 30 minutes or until the edges look dry and middle looks set. The best thing about these brownies is they are eggless, so if you like super soft and fudgy brownies, feel free to bake less.
Once the brownies cool, transfer to the freezer until they are firm.
To make the ice cream: In the bowl of a stand mixer fitted with the whisk attachment, add the heavy whipping cream. Mix, starting on low to avoid splattering, then gradually increase the speed. Continue to whisk until you are at full speed and stiff peaks form. (If you are making a flavor, you may add the strawberry powder, raspberry powder, cocoa, coffee, vanilla, or mint extract here).
Add in the sweetened condensed milk. Stir to combine into a smooth batter. (If you are folding in sprinkles or chocolate chips, do that now). Set aside.
Line a 9x13-inch baking pan with parchment paper. Let the parchment paper fold over the sides for easier removal.
Remove the brownies from the freezer and cut them in half. Place one half into the baking pan, it should fit almost perfectly.
Transfer the ice cream mixture on top of the brownies in the pan and spread evenly.
Drop dollops of caramel swirl (or if you are using jam, do that here) and then swirl it into the ice cream.
Top with the second brownie half.
Freeze overnight.
Cut into 12 bars (or any size you like!).
Wrap bars in plastic wrap and store in the freezer.