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Peel and core your fresh pineapple. Slice into thick ½-inch rings. Pat dry each piece with paper towels to remove excess moisture.
In a large bowl, whisk together flour, sugar, baking powder, salt, and cinnamon. Add the egg and milk, stirring until smooth.
Pour vegetable oil into a deep pan or fryer, about 2 inches deep. Heat over medium-high until it reaches 375°F (190°C).
Dip each pineapple ring into the batter, coating it evenly. Let excess batter drip off. Carefully place each coated ring into the hot oil using tongs. Fry 2–4 minutes per side until golden brown.
Remove fritters and transfer to a paper towel–lined plate to drain oil. While still warm, dust them generously with a cinnamon sugar mix.
Serve immediately. Pineapple fritters taste best fresh, while still crisp and slightly warm.