Grease a waffle iron with cooking spray and preheat according to manufacturer's instructions.
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Whisk flour, sugar, baking powder, and salt together in a large bowl.
Whisk milk, beaten eggs, butter, and vanilla extract together in a separate bowl. Pour over flour mixture; stir until batter is just moistened.
Scoop 2 teaspoons of batter into the waffle iron for each waffle pop, leaving space between each one. Insert a lollipop stick 3/4 of the way into each pool of batter. Close lid; cook until golden and crispy, about 1 minute. Transfer waffle pop to a cooling rack. Repeat with remaining batter and lollipop sticks.
Melt white chocolate in a microwave-safe glass or ceramic bowl in 15-second intervals, stirring after each interval, 1 to 3 minutes.
Scoop melted chocolate into a pastry bag fitted with a small writing tip or into a plastic resealable bag with a corner snipped off. Drizzle chocolate over one side of the waffle pops.
Sprinkle candy sprinkles and colored sugar over pops while chocolate is still warm. Let cool until chocolate firms up, about 5 minutes.
All waffle irons are built differently and will affect the batch size. My circular waffle iron was able to close over waffle pops baked in the 2 front sections only, so I was able to make 2 at a time. Your batch size may vary.
79.19 calories; 1.33 g protein; 8.98 g carbohydrates; 0.1 g dietary-fiber; 6.17 g sugars; 4.27 g fat; 2.33 g saturated-fat; 15.06 mg cholesterol; 70.98 IU vitamin-a-iu; 0.41 mg niacin-equivalents; 0.01 mg vitamin-b6; 0.01 mg vitamin-c; 8.21 mcg folate; 35 mg calcium; 0.26 mg iron; 1.86 mg magnesium; 22.01 mg potassium; 59.37 mg sodium; 0.03 mg thiamin; 38.4 calories-from-fat; 45 percent-of-calories-from-carbs; 48 percent-of-calories-from-fat; 6 percent-of-calories-from-protein; 26 percent-of-calories-from-sat-fat