Whisk the chocolate pudding mix with the cold milk in a large bowl for 2 minutes until thickened, then refrigerate 10 minutes to fully set.

In a separate bowl, beat the heavy cream, powdered sugar and vanilla with a mixer on high 3 to 4 minutes until stiff peaks form that hold their shape.

Fold half the whipped cream into the set pudding to lighten it, keeping the remaining whipped cream separate for the top layer.

In a large trifle bowl or glass serving bowl, layer one third of the brownie cubes across the bottom.

Spoon one third of the chocolate pudding mixture over the brownies, spreading to the edges.

Sprinkle with 1/4 cup crushed candy canes.

Repeat the layers two more times: brownies, pudding, candy cane sprinkle.

Top the final layer with the reserved plain whipped cream, spreading or piping it to the edges.

Scatter the remaining crushed candy canes and mini chocolate chips over the top.

Cover and refrigerate at least 4 hours, or up to 2 days, so the brownies soften slightly and the layers set before serving.