Set aside a few strawberries for garnish. Hull and thinly slice remainder of berries. Whip the 3 cups of cream to stiff peaks. Add powdered sugar and vanilla; continue whipping until well combined. Spread thin layer of whipped cream on the bottom of a 9x13-inch baking pan. Completely cover this with cookies. Lightly cover this cookie layer with more whipped cream and then a single layer of strawberries. Add more whipped cream, then cookies, and then berries. Continue layers until all cookies, cream, and berries are used.
In a small saucepan, heat the 1/4 cup cream until bubbles form around the edges. Add chopped chocolate. Let stand for a few minutes, then whisk until the mixture is thick and glossy. Drizzle this over the layered dessert with a spoon, or transfer to a squeeze bottle for drizzling. Refrigerate overnight. The cookies should soften completely. Garnish with additional berries if desired.
This Strawberry Shortbread Trifle recipe is from the 101 Things To Do With A Casserole Cookbook. Download this Cookbook today.