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When ready to cook, start the Traeger on Smoke with the lid open until a fire is established (4-5 minutes). Turn temperature to 350 degrees F and preheat, lid closed, for 10 to 15 minutes.
Pour melted butter into a 12-inch cast iron pan. Sprinkle brown sugar on top of the butter. Arrange pineapple slices on brown sugar, squeezing in as many slices as possible. Place a cherry in center of each pineapple slice; press gently into brown sugar.
Make cake batter as directed on box, substituting pineapple juice mixture for as much of the water as possible, and adding in required oil and eggs. Pour batter into cast iron dish, over pineapple and cherries.
Place the cast iron pan on the grill grate and cook for 20 minutes. Rotate the pan a half turn to ensure it cooks evenly. Cook for an additional 20 minutes, or until toothpick inserted in center comes out clean.
Immediately run knife around side of pan to loosen cake. Place heatproof serving plate upside down onto pan; turn plate and pan over.
Leave pan over cake 5 minutes so brown sugar topping can drizzle over cake. Cool 30 minutes. Enjoy!