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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
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2 Answers

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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You need to have a good amount of caramel to keep them in place, also it seems like your batter isn't runny enough. Also turn it upside down immediately after coming out of the oven that should help too!I cook mine in a 12 inch cast iron skillet that has been seasoned. (Can purchase at Walmart pre-seasoned)Here is a NO FAIL recipe I always use and I have never had a problem with the pineapple not coming out beautifully! Good luck! http://theview.abc.go.com/blog/rees-pioneer-woman-recipes-sweets

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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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