Pulse Oreos and dehydrated strawberries in a food processor until finely crushed. Alternatively, place in a large ziplock bag and crush with a rolling pin until fine crumbs.

In a large bowl, whisk together cheesecake pudding and milk. Whisk until smooth. Fold in diced strawberries. Set aside to set for 5 minutes.

Place a spoonful of oreo strawberry crumbs at the bottom of each cup. Add a layer of pudding, then top with more crumbs followed by another layer of pudding. Chill until ready to serve.

Right before serving, top with a tablespoon of softened cool whip. Garnish with oreo strawberry crumbs and top with a strawberry slice, if desired.