Place chocolate in a metal bowl. Bring cream to a boil in a small, heavy saucepan and pour over chocolate. Let stand for 3-5 minutes then stir until smooth. Add port, stirring to combine. Remove half the chocolate mixture to a separate bowl, cover loosely with plastic wrap and place bowl in a larger bowl filled with ice to chill just until mixture reaches spreading consistency.
Spread about a teaspoon of chocolate mixture onto the bottom of a cookie. Nest three raspberries in the chocolate, pressing gently to adhere. Drizzle with some of the still-warm chocolate mixture and let stand until firm.