To start, place the bowl, whisk and heavy whipping cream in the freezer for 5 to 10 minutes. This is *optional* but I love to do this while I'm getting out the sugar and extract. It will give you a head start.
Place the cold, heavy whipping cream in the bowl of an electric-stand mixer fitted with the whisk attachment. Whisk on medium speed until medium-soft peaks form. This should take just 2 to 3 minutes. The whipped cream will be soft, smooth and barely hold its shape. Sprinkle confectioners’ sugar over the top and whisk on medium until medium-soft peaks return, taking care not to over whip the cream. This should take about 1 minute more.
If making stable whipped cream (see note below) stream the liquid gelatin mixture in while whisking on low. Add in the vanilla extract, stirring with a spatula to combine.
Place the whipped cream in an air-tight container and stash in the fridge until ready to use.