Wash the strawberries and pat them completely dry so the chocolate sets properly. Slice off the tops and carefully hollow out the centers using a small spoon. If you’d like, trim the bottoms slightly so the strawberries can stand upright as you work.
Place your chocolate and coconut oil in a microwave-safe bowl and heat in short intervals until smooth. Hold each strawberry by the top and dip the base into the melted chocolate, allowing the excess to drip off before setting them on parchment paper to dry.
Beat the softened cream cheese, powdered sugar, and vanilla until creamy. Taste and adjust sweetness if needed. Transfer the mixture into a piping bag and fill each hollowed strawberry generously. Let the chocolate firm up, and enjoy immediately or chill until serving.