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Preheat oven to 350 degrees.
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Butter half pint mason jars and sprinkle 2 tablespoons of sugar over hulled and halved strawberries.
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Sift flour, baking powder, and salt together into a medium bowl.
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Put butter and 1 cup sugar in the bowl of an electric mixer fitted with the paddle attachment and mix on medium-high speed until pale and fluffy, about 3 minutes.
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Reduce speed to medium-low; mix in egg, milk, and vanilla.
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Reduce speed to low; gradually mix in flour mixture.
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Once well mixed, spoon sugared strawberries into buttered mason jars.
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Top strawberries with cake batter, filling the mason jar only half full.
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Evenly space mason jars on a baking sheet and bake until the cake is dark golden brown, about 45 minutes. Let cool on a rack at least 30 minutes before serving. If not serving right away, let the crisps cool to room temperature, cover, and refrigerate for up to 4 days.