Line a 9×9-inch baking dish
Spread ¼ cup of thawed whipped topping into the bottom
Dip half the chocolate Oreos, one at a time, in whole milk to soften edges
Arrange dipped cookies flat in the baking dish
In a stand mixer or medium bowl, beat cream cheese, granulated sugar, almond extract, and vanilla extract for 1½–2 minutes until smooth
Fold in 1¼ cups cherry pie filling, then 3 cups of thawed whipped topping
Set aside half the mixture
Spread half the cream cheese mixture over the Oreo layer
Repeat the milk-dipped Oreo layer and remaining cream cheese mixture
Evenly spread the remaining ¼ cup whipped topping over the cream cheese layer
Cover and chill at least 6 hours or overnight
Before serving, spread remaining cherry pie filling over the whipped topping
Slice into 12 squares (4×3) and serve