Recipe

Make the Forgiving Flaky Tart Crust:

1. Preheat the oven to 350°F (175°C). Lightly butter a 9-inch (23 cm) tart pan.
2. In a food processor (see Note), place the flour, sugar, and salt and process until combined, about 5 seconds. Add the butter and vanilla to the food processor and pulse until it has a coarse but evenly moist sand texture, about 12 to 14 pulses. Crumble the dough into the prepared tart pan and press into an even layer over the bottom and up the sides. Prick the surface of the dough a few times with a fork and place in the freezer for 15 minutes to chill.
3. Bake the tart crust until golden brown, about 15 minutes. Transfer the tart pan to a wire rack and let it cool completely before adding the plums. Keep the oven on and increase the temperature to 375ºF (190ºC).

Make the Plum Port Filling:

1. In a large skillet over high heat, bring the port to a boil. Add ½ cup (105 grams) brown sugar and the anise seeds. With a spoon, continuously swirl the port in a circle until it has reduced to ⅔ cup (160 mL) of thick-as-honey syrup. This will take about 15 minutes. Any shorter and you will likely end up with a thin syrup and a soggy bottom.
2. Place the plums into a large mixing bowl. Sprinkle the flour over the plums and toss to coat. Drizzle the thick port syrup over the plums and toss again until the plums are nice and sticky. Arrange the gooey coated plums evenly in the cooled, baked tart crust. If there is remaining syrup in the bowl, now is your chance to drizzle it over the plums.

Bake the Tart:

1. Bake the tart until the juices are bubbling, the fruit is tender, and the crust is golden, 30 to 35 minutes. Transfer to a wire rack to cool and allow the filling to set for 10 minutes, then remove the tart from the tart pan (if you decide to remove the tart—serving in the tart pan works just as well). Plum port tarts are equally delicious the next day. Store in an airtight container or tightly wrapped in plastic wrap in the refrigerator for up to 4 days.