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I made an upside-down pineapple cake. It consisted of a layer of buttered caramel, a layer of pineapple pieces, and a layer of batter, baked together. I pressed the batter between the pineapple pieces before baking, hoping that it will "flow in" and keep them in place, but the pineapple was already sunk into the caramel, and it seems to have gotten quite moist during the baking. Result: when I turned the cake, half the pineapple pieces fell off. I replaced them, but I am not sure they will stay in place, even when the caramel hardens a bit, because there is no caramel between the pineapple surface and the cake.

How could I have kept them in place?

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I thought that they were cooked with the gooey bit on the bottom, then when everything was cooked it was flipped, voila upside-down rubble-double-bubble-cake! – Doug Mar 31 '12 at 6:34

Instead of worrying about how well the pineapple is sticking to the cake, I'd try different pan preparations to make sure the pineapple doesn't fix itself to the pan.

Looking at the recipe that Holly linked to -- it says specifically not to stir the butter and sugar together, which I assume would give you a better separation as there's butter against the pan, and you're doing it in a pre-heated pan, which helps to prevent sticking (but normally isn't done for most other cakes, as it'll cause them to dome on top)

If you're not making the caramel in the same pan (and so you wouldn't have that layer of melted butter), I'd be inclined to use a parchment circle with another layer of fat over it, so after you invert, you'd then have to remove the parchment (which shouldn't be too bad if done quickly, before the caramel sets)

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Spray your pan (cake pans, muffin tins) with butter flavored non stick spray (pans should stay cold or room temperature, do not preheat the pan) Add brown sugar (for this recipe in muffin tin, I used 1 teaspoon) first, then a thin slice(s) of butter. I am making mine in a large muffin tin (6 servings and dark coated non-stick) Add Pineapple and cherry next. Be sure to dry the pineapple off really well. Pour cake batter on top (use pineapple juice instead of water in your cake batter) Cook at 350 degrees in preheated oven. Cool for 15 minutes then flip onto a cookie sheet.

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I guess that could work, but in my case, the recipe involved a thick layer of caramel made separately, not just a bit of brown sugar. Still, thank you for sharing, maybe it's the solution for people who are OK with less caramel. – rumtscho Jan 3 at 14:11

You need to have a good amount of caramel to keep them in place. It also seems like your batter isn't runny enough. Turning it upside down immediately after coming out of the oven should help too! I cook mine in a 12 inch cast iron skillet that has been seasoned. (It can be purchased pre-seasoned at Walmart.) Here is a no fail recipe from The Pioneer Woman which I always use. I've never had a problem with the pineapple not coming out beautifully!

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My recipe explicitely stated to put the caramel on the bottom, then the fruit, then the batter - so there is no caramel between the fruit and the batter to glue them. And really, if it is a cake and not a quickbread, I am happy when the batter is not runny - it means it is well aerated and will make for a better cake. – rumtscho Mar 31 '12 at 12:56
    
Yes the recipe I sent you also says to put the caramel first then the fruit next then the batter. A runny batter helps hold the fruit to the cake so when you flip it, it stays in better. I agree the cake is a little more dense than a quick bread would be. But it is still really yummy! Mayabe use a little more caramel than your recipe calls for? Again, good luck! – Holly Ferdig Hennessy Apr 2 '12 at 0:16

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