Preheat oven according to brownie mix instructions. Prepare brownie mix in a large mixing bowl, pour into a greased pan and bake for 20-25 minutes. Cool completely before cutting into squares.

Rinse fresh strawberries under cold water, remove stems, and slice into pieces.

Whisk together milk and instant vanilla pudding mix in a bowl until thickened, about 2 minutes. Fold in Cool Whip until smooth.

Layer half of brownie squares in a trifle bowl. Spread half of the pudding mixture over brownies, followed by half of the sliced strawberries.

Repeat layering with remaining brownie pieces, pudding mixture, and sliced strawberries on top.

Melt chocolate chips and drizzle over the top layer of strawberries.

Cover loosely and refrigerate for at least 1 hour before serving.