Preheat oven to 350 degrees F. Grease 13x9-inch baking dish.
In a microwave-safe bowl, use a spoon to mix cocoa and oil. Add butter and melt in the microwave, 1 minute on high power.
Cool slightly. Add sugar and eggs, stir well.
Add flour, baking powder, and salt to the chocolate mixture. Stir just until combined.
Stir in chocolate chips and vanilla.
Spread half of the batter into a greased 13x9-inch pan.
In a small microwave-safe bowl, melt 50 caramels and 2 tablespoons milk on high power for 30 seconds at a time, stirring often, until caramel sauce is melted and smooth.
Pour caramel sauce evenly over brownie layer. Spread remaining brownie batter over caramel.
Bake uncovered for about 30 minutes until a toothpick inserted into the center comes out with a few moist crumbs.
Remove from oven and allow to cool about 30 minutes.
In a small microwave-safe bowl, combine 15 caramels and 1 tablespoon of milk and heat on high power for 30-second intervals, stirring often, until caramel sauce is melted and smooth.
Drizzle caramel sauce over brownies. Cool completely before cutting.