Step 1: Preheat the oven to 325 F.
Step 2: Grease bottom of a 9x9-inch baking pan.
Step 3: Combine the graham crumbs with 1/2 cup melted butter. Measure out 2 cups of the crumb mixture (set aside the remaining crumbs) press the 2 cups of crumb mixture firmly into the pan. Bake for 8-10 minutes. Place on wire rack to cool completely (about 30-40 minutes).
Step 4: In a bowl using an electric mixer, beat the cream cheese and 1/2 cup soft butter together until creamy. Turn the mixer down to low and add the in the powdered sugar 1 cup at a time until incorporated. Increase speed and beat well for a minute or so. Using a spatula, mix in 2 heaping tablespoons of the drained crushed pineapple into the creamed mixture (SEE MY NOTE ON BOTTOM OF INSTRUCTIONS).
Step 5: Spread the cream cheese and pineapple mixture over the cooled crust. Refrigerate for 1 hour (or longer).
Step 6: Meanwhile in a bowl using a spatula combine all the remaining drained crushed pineapple into the thawed Cool Whip, then using a spoon dollup over the cream cheese mixture then gently spread it out. Sprinkle the remaining reserved graham cracker crumb mixture on top. (if your using an 8x8 pan your pan will be quite full). Refrigerate for at least 4 hours, preferably overnight.
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