In a mixing bowl, combine the dark rum, brown sugar, and vanilla extract. Add the pineapple slices and let them soak for at least 10 minutes.

Heat the vegetable oil in a frying pan over medium heat.

Remove the pineapple slices from the rum mixture, allowing excess liquid to drip off. Dredge each slice in flour, shaking off the excess.

Carefully place the coated pineapple slices in the hot oil and fry for about 2-3 minutes on each side, or until golden brown.

Remove the fried pineapple and place it on paper towels to drain excess oil.

Dust with cinnamon and powdered sugar before serving.