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1. In a medium, heavy-bottomed saucepan, combine the uncooked rice and 2 1/2 cups of the milk. Give it a gentle stir so the rice doesn’t clump on the bottom.
2. Set the pan over medium heat and bring the mixture just up to a gentle simmer, stirring occasionally so the rice doesn’t stick. Once it starts to bubble around the edges, turn the heat down to low so it simmers softly.
3. Cook, uncovered, stirring often, until the rice is tender and the mixture has thickened, 25–35 minutes. As it cooks and thickens, add the remaining 1/2 cup milk a little at a time if the pudding seems too thick or the rice isn’t quite soft yet.
4. When the rice is tender and the pudding is creamy but still a bit loose (it will thicken more as it cools), stir in the sugar. Keep stirring over low heat for another 3–5 minutes, until the sugar is fully dissolved and the pudding is silky.
5. Remove the saucepan from the heat and stir in the vanilla extract. Taste and adjust the sweetness if you like, adding a spoonful more sugar if needed while the pudding is still warm so it dissolves easily.
6. Let the pudding sit for 5–10 minutes to thicken slightly, stirring once or twice to keep a soft, creamy texture. Serve warm for the coziest experience, or transfer to a bowl, press a piece of plastic wrap directly on the surface to prevent a skin from forming, and chill if you prefer it cold.
7. If the pudding thickens too much as it cools, simply stir in a splash of milk before serving to loosen it back to a creamy consistency.
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