In a medium saucepan over medium heat, whisk together the coconut milk, sweetener, and espresso powder until sweetener has dissolved. Bring to a simmer.
Remove from heat and add chopped chocolate. Let sit 4 minutes until chocolate is melted, then whisk until smooth. Whisk in vanilla extract.
In a blender or food processor, combine avocados, chocolate mixture, cinnamon, and chipotle. Puree until smooth. Refrigerate until cool, at least 2 hours.
Transfer mixture to an ice cream maker and churn until consistency resembles soft serve ice cream (this takes less time than custard based ice creams). Serve as soft serve or transfer to an airtight container and freeze another few hours for a firmer consistency.