Chop your dark chocolate bar into irregular chunks. Make some pieces small and some pieces slightly larger. Set the chocolate and cherries aside in the fridge.

Grab your large mixing bowl and a sturdy whisk. Pour in the milk and the granulated sugar together. Whisk until you can no longer see sugar grains.

Stir in the heavy cream and the vanilla extract. Mix gently so you do not create too many bubbles. The mixture should look very smooth and white.

Pour the liquid into your cold ice cream maker. Turn the machine on and let it churn. Follow the timing in your specific machine manual.

Wait until the cream looks like soft-serve ice cream. This usually takes about twenty to twenty-five minutes. Do not let it get too hard yet.

Add the chilled cherries and chocolate chunks slowly now. Let the machine mix them for two more minutes. This spreads the treats evenly through the cream.

Turn off the machine and grab your storage container. Scoop the soft ice cream into the container quickly. Smooth the top with your silicone spatula.

Cover the container with a tight lid or wrap. Place it in the back of your freezer. Let it firm up for at least six hours.