Bring a small pan with 1 inch of water to a boil over medium-low heat. Place the chocolate in a small bowl and place over the simmering water. When the chocolate is almost halfway melted, remove the bowl from the heat to a towel. Continue to stir with a rubber spatula until completely melted.
Spoon 1 teaspoon of chocolate into each of 12 cavities in a silicone mini muffin mold. Swirl the mold over a rimmed baking sheet to coat the sides of each mold. Chill in the refrigerator to set completely, about 45 minutes.
Meanwhile, whisk together the cream, sugar and vanilla. Carefully unmold the chocolate cups and trim any excess with kitchen scissors. Fill each cup with a spoonful of strawberries and a dollop of cream. Serve immediately.