Line a baking sheet with parchment paper and set aside.
Rinse strawberries and pat them dry. Remove the tops and hull the center using a small paring knife.
1 pound (about 12-15) large strawberries
Place chocolate chips in a microwave-safe bowl. Heat in 30-second intervals, stirring between each until completely melted.
6 ounces (1 cup) semi-sweet chocolate chips
Dip each strawberry in melted chocolate. Place on the parchment-lined baking sheet to set. While the strawberries set, prepare the cheesecake filling.
In a large bowl, combine softened cream cheese, powdered sugar, and vanilla extract. Use a hand mixer to blend until smooth. Add heavy cream and beat for an additional 2 minutes until light and fluffy. Place the bowl in the refrigerator for 15 minutes to allow the filling to chill.
4 ounces cream cheese, ½ cup powdered sugar, ¼ cup heavy cream, 1 teaspoon vanilla extract
Transfer the chilled cheesecake filling to a piping bag with a tip. Pipe some filling into each chocolate-covered strawberry.
If the filling seems soft, place strawberries in the refrigerator for 10-15 minutes to set the cheesecake filling.
Serve immediately or within 12 hours for the best texture and flavor.