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Line an 8×8-inch baking dish with parchment paper, including up the sides of the dish.
In a medium bowl, combine shortbread crumbs and melted butter with a fork. Mix until all ingredients are fully incorporated with no dry spots.
Press the crumbs firmly into the bottom of the lined baking dish.
To a large bowl, add cream cheese, confectioners' sugar, vanilla, and lemon juice. Using a hand mixer on medium speed, beat until creamy, about 3 minutes.
Mix in 2 cups of whipped topping.
Top the crust with half of the cream cheese mixture.
To the remaining cream cheese mixture, mix in ¼ cup of the cherry jello mix.
Add the cherry jello mixture to the top of the cream cheese mixture.
Top with remaining whipped topping and the cherry pie filling.
Place in the refrigerator to chill for 1 hour, up to overnight.