1. Prepare the Pudding:

• In a medium bowl, whisk the chocolate pudding mix with cold milk until well combined.
• Refrigerate for about 5 minutes until thickened but still spoonable.

2. Make the Whipped Cream:

• In a large chilled bowl, beat the heavy whipping cream, powdered sugar, and vanilla extract until soft peaks form.
• Continue beating until firmer peaks develop, being careful not to overwhip.
• Set aside in the refrigerator.

3. Prepare the Cream Cheese Layer:

• In a separate bowl, beat the softened cream cheese and granulated sugar until smooth and fluffy, about 2 minutes.
• Gently fold in half of the prepared whipped cream until well combined but still light and airy.

4. Crush the Cookies:

• Place Oreo cookies in a ziplock bag and crush using a rolling pin, creating a mixture of fine crumbs and some larger pieces for texture.
• Leave the cream filling intact as you crush the cookies.

5. Assemble the Trifle:

• In a trifle dish or large clear glass bowl, begin with a layer of crushed Oreos on the bottom.
• Add a layer of the cream cheese mixture, spreading it evenly to the edges.
• Follow with a layer of chocolate pudding.
• Add a layer of the reserved whipped cream.
• Repeat the layers until you reach the top of your dish, finishing with a layer of whipped cream.

6. Garnish & Chill:

• Sprinkle the remaining crushed Oreos over the top layer of whipped cream.
• For an extra special touch, arrange a few whole Oreos decoratively on top.
• Cover lightly with plastic wrap and refrigerate for at least 1 hour before serving, though 3-4 hours is ideal for the best flavor development.