Add strawberries and sugar to a small pan and bring to a boil over medium heat. Lower heat to a simmer for 5 minutes or until strawberries are tender. Remove from heat.
Add milk to the strawberries and blend with an immersion blender until smooth. Set aside.
Using a matcha whisk or milk frother, whisk matcha into the hot water until smooth and no lumps remain. Mix in vanilla syrup, if desired.
Add ice to 2 serving glasses. Divide strawberry milk evenly between the glasses, then gently pour the prepared matcha over the strawberry milk. Serve immediately.
Notes
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