Pick through the strawberries and use a small knife to hull each one, removing the green leaves and core, revealing a hollow center. Arrange on a plate for filling.
In a mixing bowl, combine the softened cream cheese, powdered sugar, and vanilla extract. Use a spoon to blend until smooth and creamy, with no lumps. Smooth the mixture into a piping bag or plastic zip-top bag with the tip cut off.
Pipe the cream cheese filling into each hollowed strawberry, filling them generously until overflowing slightly. Place the filled strawberries on a tray.
In a microwave-safe bowl, combine chopped chocolate and vegetable oil. Microwave in 30-second intervals, stirring after each, until the chocolate is fully melted and smooth. The mixture should be glossy and free of lumps.
Using a fork or dipping tool, hold each stuffed strawberry and dip the top into the melted chocolate, allowing excess to drip off. Place the dipped strawberries on a parchment-lined tray and refrigerate for about 10-15 minutes until the chocolate sets and firms up.
Once the chocolate has set, arrange the strawberries on a serving plate. Optional: drizzle additional melted chocolate over the strawberries for decorative effect. Serve immediately or keep refrigerated until ready to serve.
