The chocolate crumb is entirely optional, but is well worth the effort. It's inspired by Christina Tosi's Momofuku Milk Bar crumb recipe .
500g castor sugar
250ml sweet apple or pear cider
6 ripe pears, peeled
2 star anise
1 vanilla bean pod, halved, seeds scraped
1 cinnamon quill
100g plain flour
1 tsp cornflour
100g castor sugar
65g cocoa powder
1 tsp salt
85g butter, melted
1 cup (150g) plain flour
½ tbsp baking powder
1 cup (220g) castor sugar
½ cup (50g) cocoa powder
70g butter, melted and cooled
½ cup (125ml) milk
½ cup dark chocolate, broken into chunks
1 cup red wine
cream or vanilla ice-cream, to serve
For the poached pears add all ingredients and 500ml of water to a saucepan and bring to the boil. Once on a rolling boil and the sugar has dissolved, turn the heat to low and simmer for one and a half hours. Remove from heat and allow pears to cool in the syrup.
For the chocolate crumb preheat the oven to 180C. Mix the dry ingredients in a bowl until combined. Add the melted butter and stir until the mixture starts to come together and form small clusters. Line a baking tray with baking paper and spread the clusters out across it. Bake for 20 minutes or until fragrant. Remove from oven – the crumbs will still be slightly tacky – and allow to cool completely on the tray. Store leftover crumbs in an airtight container. They will keep for one week at room temperature or one month in fridge or freezer (makes about 2 cups).
For the pudding preheat the oven to 160C and boil the kettle. Grease a 1.5 litre (6-cup) capacity ovenproof baking dish or six 1-cup capacity ramekins.
Sift the flour, 1/2 cup of the sugar and 1/4 cup of the cocoa into a bowl, stir to combine and make a well in the centre. In a separate bowl, whisk melted butter, milk, vanilla extract and egg. Gradually pour into the well, then fold to combine.
Spread mixture evenly into prepared dish or dishes. Push the chunks of dark chocolate into the batter and smooth over the top with the back of a spoon. Combine remaining 1/2 cup sugar and 1/4 cup cocoa and sprinkle over the top of the pudding. Carefully pour one cup of boiling water over the top of the pudding, followed by one cup of red wine.
Bake for 30 to 35 minutes until the top is firm (you may need to increase the cooking time by about 10 minutes if using one large dish). Stand for 10 minutes to cool slightly.
To serve, gently remove a pear from the syrup and place in the centre of each pudding. Sprinkle over 1 to 2 tablespoons of chocolate crumb and serve with vanilla ice-cream or cream.