Whip the heavy cream in a large bowl until stiff peaks form, about 3 to 4 minutes.

Stir the drained crushed pineapple into the sweetened condensed milk until combined.

Fold the whipped cream into the pineapple mixture in three additions, then scrape into a loaf pan and cover. Freeze at least 6 hours.

Let the ice cream soften at room temperature for 5 minutes, then scoop and serve.