Combine granulated sugar and water in a small saucepan. Bring to a boil over high. Reduce heat to medium, and cook, stirring constantly, until sugar dissolves, about 5 minutes. Remove from heat, and cool completely, about 1 hour.
Process tamarind paste and 1/2 cup cooled syrup in a blender on high speed until almost smooth, about 30 seconds. Add cinnamon, 1 1/2 cups of the strawberries, and remaining syrup, and process on high speed until smooth, about 45 seconds. Finely chop remaining 1 1/2 cups strawberries, and fold into mixture in blender.
Pour mixture evenly into 10 (2-ounce) plastic ice pop molds. Freeze 1 hour. Insert pop sticks, and freeze until solid, about 3 more hours.
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