Prepare Orange Cranberry Pound Cake

1. Preheat oven to 350°F. Grease two loaf pans and coat lightly with flour. Whisk together flour, baking powder, and salt. Set aside.
2. In a large bowl, cream sugar, butter, and orange zest until fluffy. Beat in the eggs, one at a time, scraping bottom and sides of bowl as needed. Whisk milk, orange juice, and vanilla together in a glass measuring cup.
3. In three additions, mix in flour alternating with milk/orange juice. End with flour, mixing just until combined. Fold in cranberries. Pour into loaf pans and bake 50-65 minutes until tops bounce back when lightly pressed. Cool in pans 15 minutes then remove to wire cooling racks to cool completely. Can be made a day ahead of assembly and tightly wrapped in foil.

Prepare Pastry Cream 

1. In a large bowl, whisk 1/4 cup milk, cornstarch, flour, egg yolks, and vanilla. Set aside.
2. Combine remaining 2 3/4 cup of milk, sugar, and salt in a medium saucepan. Heat over medium-high heat until boiling. Remove from heat.
3. Gradually whisk about 1/2 of the hot milk into egg yolk mixture. Pour back into the pan. Heat on medium heat, constantly stirring, until mixture comes to a boil. Boil for 30 seconds then remove from heat.
4. Pour mixture through a fine sieve placed over a bowl. Once cream has gone through sieve, stir in butter until melted and combined. Let sit 10-15 minutes at room temperature.
5. Press plastic wrap directly onto cream and chill thoroughly before using. Can be made ahead 2-3 days and kept in a refrigerator.

Prepare Sugared Cranberries

1. In a small saucepan, heat 1/2 cup sugar and water over medium heat. Stir until sugar dissolves and mixture comes to a simmer. Remove from heat and cool to room temperature.
2. Set a wire cooling rack over a rimmed baking sheet. Pour cranberries into the cooled sugar syrup. Coat well. Use a slotted spoon to remove to wire rack. Reserve 1/4 cup sugar syrup for assembly. Let cranberries sit 25 minutes.
3. Pour remaining sugar onto a rimmed plate. Roll cranberries in sugar, a few at a time, until completely coated. Place on a tray to dry. Once dry, store at room temperature in an airtight container.

Assembly

1. Trim edges off of cakes and then cube into bite-size pieces. Place 1/3 of the cake pieces in bottom of trifle bowl.
2. Whisk reserved sugar syrup with Cointreau. Sprinkle 1 tablespoon over cake pieces. Dollop 1/3 of cooled pastry cream over cake. Spoon 1/3 cranberry sauce over pastry cream. Repeat layers twice more ending with cranberry sauce. Spread the whipped topping over top. Cover with plastic wrap and refrigerate 3 hours or overnight.
3. Just before serving, top with sugared cranberries and orange zest. Cover leftovers and store up to 3 days.