Make the ganache. Place the chopped chocolate in a heatproof bowl. Heat ¼ cup heavy cream until just steaming. Pour over the chocolate and let sit for 2 minutes, then stir until completely smooth and glossy.

Freeze the ganache. Pour into a 4×6 or similar small parchment-lined container, keeping the layer thick. Freeze for 2 to 3 hours, or until completely firm.

Cut into cubes. Lift the frozen ganache from the container and cut into small cubes. Return to the freezer while you prepare the bread and whipped cream.

Make the chocolate whipped cream. Add 1½ cups heavy cream, sugar, vanilla, and cocoa powder to a chilled mixing bowl. Whip until just thick and fluffy with stiff peaks. Do not over whip. Set aside.

Deep fry the milk bread. Attach a candy thermometer to a heavy medium pan or cast iron dutch oven. Add 1 inch of neutral cooking oil (avocado oil, canola oil, or grapeseed oil, etc.). Heat over medium heat until the thermometer reads 350F/176C. Add a slice of milk bread and deep fry until golden brown, about 30 seconds only per side. Remove and set aside on a plate lined with a paper towel or a cookie rack fitted over a sheet pan.

Slice each full bread slice in half on a diagonal. Create a pocket in each half using a sharp knife. Use an offset spatula or fork to form the pocket as much as you can without splitting the bread.

Add a generous layer of chocolate whipped cream inside the pocket. Arrange the frozen ganache cubes over the whipped cream, then dust generously with additional cocoa powder and serve immediately.