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Step 1
If using a shaved ice machine, fill ice molds with whole milk and place on a level surface in freezer and freeze until solid, 4–6 hours.
Step 2
If not using a shaved ice machine, pour whole milk into an 8" square metal baking pan and freeze until edges begin to set, 30–35 minutes.
Step 3
Using a fork, scrape milk to break up frozen portions. Continue to freeze, scraping and breaking up every 20–30 minutes, until mixture resembles fluffy shaved ice, 2–4 hours.
Step 4
Bring frozen strawberries and sugar to a boil in a medium saucepan over medium heat; simmer until saucy, 5–8 minutes. Remove from heat and crush berries with a potato masher or fork. Mix in lemon juice. Taste and add more lemon juice if needed. Chill strawberry sauce until cold, about 45 minutes.
Step 5
If using shaved ice machine, remove frozen milk from freezer and let thaw 5 minutes. Place into machine and shave according to manufacturer’s directions.
Step 6
To serve, place 1 Tbsp. condensed milk and 1 Tbsp. strawberry sauce into each glass. Spoon shaved ice over, dividing evenly. Top shaved ice with fresh strawberries and more strawberry sauce, then drizzle a little more condensed milk over.