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Before starting, I recommend freezing your serving cups and blender for 15 minutes. This will keep the milkshake colder for longer. Even just 10 minutes in the fridge is good.
Combine ice cream, milk, jam, and frozen strawberries in a blender. Blend on medium-high speed until everything is smooth and combined. If the milkshake gets stuck, you can use your blender's tamper to push down the ingredients. Try not to add milk though as it will get too runny.
Pour the milkshake into a tall glass and top it with whipped cream and maraschino cherries.