Prepare the angel food cake according to package directions. Let cool completely, then cut into bite-sized cubes.
In a large bowl, combine sliced strawberries, sugar, and lemon juice. Stir and let sit for 15–20 minutes until juicy.
In a bowl, whisk together vanilla pudding mix and cold milk until thickened (about 2–3 minutes).
In a separate bowl, beat softened cream cheese, powdered sugar, and vanilla extract until smooth. Fold in the prepared pudding, then gently fold in whipped topping until fully combined and fluffy.
In a large trifle dish or glass bowl, layer: cake cubes, strawberries, cream mixture. Repeat layers until ingredients are used, finishing with the cream layer on top.
Top with extra whipped topping and sprinkle crushed cookies if using.
Cover and refrigerate for at least 2 hours (or overnight) before serving.
Scoop into bowls and serve chilled.