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Preheat the oven to 350°. Measure 4 cups of pretzels, then place inside a ziploc bag. Crush the pretzels into coarse crumbs with a rolling pin.
In a mixing bowl combine the pretzel crumbs, melted butter, and granulated sugar.
Use the bottom of a measuring cup to press this mixture into the bottom of an ungreased 9x13 inch baking dish. Bake for 10 minutes. Remove the pan from the oven and allow it to cool completely.
In a large mixing bowl, use an electric mixer to beat the cream cheese, sugar, and vanilla extract on medium speed until fluffy, about 1-2 minutes.
Gently fold in the cool whip, using a spatula until well combined.
Spread the mixture evenly over the cooled crust, ensuring that it reaches the edges of the pan to prevent the strawberry topping from seeping into the crust. Cover the pan and place it in the refrigerator for one hour.
Slice fresh strawberries and measure out 4 cups.
In a mixing bowl, whisk the jello and boiling water until the jello completely dissolves.
Add the sliced strawberries to the mixture and combine. Spoon the jello mixture directly onto the filling and spread it evenly to create a smooth layer. Pour the remaining jello liquid over the strawberries.
Cover the pan again and refrigerate for a minimum of 6 hours.
To serve, cut into slices.