Add the fresh cranberries and granulated sugar to a food processor. Pulse in quick bursts until the cranberries are finely chopped but not pureed—you still want tiny bits, not a smooth sauce. Scrape down the sides once or twice so everything chops evenly.
12 oz fresh cranberries, 1 cup granulated sugar
Transfer the chopped, sugared cranberries to a bowl. Stir well, cover, and refrigerate for at least 30 minutes and up to 2 hours. This softens the berries and creates a ruby syrup that sweetens the salad.
12 oz fresh cranberries, 1 cup granulated sugar
While the cranberries rest, drain the crushed pineapple very thoroughly. Place it in a fine-mesh strainer set over a bowl and press gently with the back of a spoon to remove as much liquid as possible so the salad can set properly.
20 oz crushed pineapple
In a small heatproof bowl, add the raspberry or cherry gelatin. Pour the boiling water over it and stir until the gelatin is completely dissolved. Let it cool to room temperature or just warm so it doesn’t melt the creamy mixture later.
3 oz raspberry or cherry flavored gelatin, 3/4 cup boiling water
In a large mixing bowl, beat the softened cream cheese with an electric mixer until smooth and fluffy, 2–3 minutes. Add the sour cream or Greek yogurt, vanilla, and a pinch of fine sea salt. Beat again until very smooth and well combined.
8 oz cream cheese, 1 cup sour cream or plain Greek yogurt, 1 teaspoon pure vanilla extract, 1 pinch fine sea salt
In a separate chilled bowl, whip the heavy cream to soft-to-medium peaks—light and airy, not stiff. If using prepared whipped topping instead, have 2 cups measured and ready and skip whipping.
1 cup heavy whipping cream
With the mixer on low, slowly drizzle the cooled gelatin mixture into the cream cheese mixture. Scrape down the bowl and continue mixing until fully blended. The mixture should be pale pink and slightly loose.
3 oz raspberry or cherry flavored gelatin, 3/4 cup boiling water, 8 oz cream cheese, 1 cup sour cream or plain Greek yogurt, 1 teaspoon pure vanilla extract, 1 pinch fine sea salt
Gently fold the macerated cranberries (along with their syrup), the well-drained crushed pineapple, and the chopped nuts into the creamy gelatin base using a rubber spatula. If using mini marshmallows, diced apple, or orange zest, fold them in now as well.
12 oz fresh cranberries, 1 cup granulated sugar, 20 oz crushed pineapple, 1/2 cup chopped walnuts or pecans, 1/2 cup mini marshmallows, 1/2 cup finely diced apple, 1 zest of 1 orange
Fold the whipped cream into the mixture in two additions, using a light hand to keep it fluffy. Taste and, if desired, add an extra tablespoon or two of sugar (not listed) and fold again for sweetness.
1 cup heavy whipping cream
Pour the cranberry salad mixture into a 2–2.5 quart serving dish, glass bowl, or an 8×8 or 9×13-inch dish if you prefer squares. Smooth the top, cover, and refrigerate for at least 4 hours or overnight, until softly set and scoopable.
Just before serving, garnish with extra chopped nuts, a few fresh cranberries, or orange zest if desired. Serve well chilled. The texture should be creamy and fluffy with bits of fruit and nuts, not firm like plain gelatin.
additional chopped nuts, fresh cranberries, or orange zest