Instant Pot: If cooking in the Instant Pot or pressure cooker, skip the soaking time.
Start by lightly brushing the bottom of your pot with vegetable oil. Add the tapioca pearls and the water.
Lock the lid, turn the valve to sealing, and set to cook on High Pressure (press the pasta button) for just 3 minutes.
Then do a quick release of pressure after 10 minutes has passed. You will notice some pearls will still be opaque while others will be translucent. But most of them will be almost ‘al dente’.
Using a wooden spoon, stir the mixture very well, sometimes slightly pressing them against the sides of the pot to separate them. But do not mash them! If some stick in the bottom of the pot, you will be able to get most out once the final dessert has cooled almost completely in the pot.
Add the wine (or grape juice or half of each), sugar, cinnamon stick, and cloves to the pot. Stir and press the sauté button.
Let it cook for about 12-15 minutes, stirring every once in a while, or until most of the pearls are translucent. Remove the cinnamon stick (and if possible, the cloves).
Serve this Instant Pot tapioca pudding warm, at room temperature, or chilled with vanilla ice cream or crème Anglaise.
Stovetop: Soak the pearls in water for about 45 minutes either in a bowl or in the no stick saucepan that you will use to cook the pudding. Do not drain!
Add the red wine, sugar, cinnamon stick, and cloves. Stir well until the sugar is dissolved and comes to a boil over medium-high heat.
Then, reduce the heat to medium and cook for about 20-30 minutes or until the pearls are soft and several are translucent. Make sure to stir every once in a while!
Transfer to glasses, ramekins, or a bowl. Serve warm, at room temperature, or chilled with vanilla ice cream or crème Anglaise.
Crème Anglaise Recipe: In a medium heavy bottomed saucepan, add the cream, milk, 1/3 cup of sugar, and both the vanilla pod and beans. Simmer over medium heat for about 2 minutes or until the mixture starts to bubble around the edge of the pan. Please do not let it boil!
Remove the pan from the heat and let sit for 20 minutes. While the dairy mixture is infusing, whisk the egg yolks with the remaining 1/3 cup of sugar in a medium bowl until it turns pale. Remove the vanilla pod and discard!
Using a ladle, pour a ladle of the warm cream mixture into the egg yolk mixture, then swiftly whisk to combine. Add another ladle of the infused mixture to the egg mixture until it is warm to the touch. This method is called tempering and it is essential to prevent the yolks from curdling.
Pour the tempered cream and egg mixture into the remaining dairy mixture in the saucepan, then return the pan to the heat. Cook over medium heat, stirring constantly, for about 5-7 minutes or until the custard coats the back of a spoon.
Once the custard has thickened, remove from heat and strain through a sieve into a medium bowl. This will remove any lumps and the custard will be smooth. Cover the surface of the custard with plastic wrap to remove air and prevent the formation of a thick skin. Then chill in the fridge for about 2 hours before serving. Or keep refrigerated for up to 4 days!