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Preheat oven to 160°C/320°F (140°C fan) with shelf in the middle.
Pile strawberries on a tray. Sprinkle over sugar. Toss through, then spread strawberries out on tray.
Roast for 45 minutes, rotating tray halfway. Remove from oven, toss strawberries, then return to oven for 15 minutes. Keep an eye on it - don't want juices to become toffee and stick to tray.
Remove from oven, use spatula to scrape into a food processor, being sure to get all the juices and caramelised bits off the tray.
Blitz until smooth as possible (caramelised bits won't blitz smooth), scrape into bowl then cool completely.
Add condensed milk and vanilla into strawberries. Beat well for 1 1/2 minutes on high to aerate and combine.
Place cream in another bowl. Use electric beater to beat into stiff peaks - about 3 minutes on high.
Add a dollop of cream into the strawberry mixture. Fold through gently, don't beat in furiously (see video for technique). When mostly mixed through, add another dollop and for through about 5 times.
Tip strawberry mixture into the cream bowl. Gently fold through until it's a uniform pink colour - about 15 to 20 folds max. Some streaks is ok.
Pour mixture into a container (preferably glass with airtight lid), smooth top.
Place sheet of baking paper on surface and press out air bubbles (stops icicles forming). Cover with lid, freeze 12+ hours.
Remove from freezer, remove paper. Scoop with ice cream scooper and serve in cones or bowls!