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Place a medium-sized bowl (preferably metal) in the freezer for at least 10 minutes to chill.
Once bowl has chilled, remove from freezer and add heavy cream, powdered sugar, and vanilla extract.
Using an electric mixer², beat ingredients on low speed, gradually increasing speed to high, and beat until stiff peaks form. Don't over-beat, but don't stop beating until cream has reached a thick, billowy consistency (think the thickness of Cool Whip).
Keep unused whipped cream refrigerated in an airtight container.