Old-Fashioned Pineapple Upside Down Cake
Nothing says "special occasion, 1965" like the flip. A pineapple upside down cake was granny's party trick — bake, count to five minutes, one confident turn of the wrist, and the plainest sponge in her repertoire came out dressed in glossy caramel, golden rings and cherries like jewels.
Two things decide whether the flip goes your way. First, dry the pineapple rings properly — wet fruit waters the caramel down into syrup that soaks the sponge. Second, flip at exactly five minutes: sooner and the caramel's still molten and slides off; later and it sets to the tin like glue. Five minutes. Granny used to stand over it with the clock.
Serve it warm with cream or custard, and accept that the cherry-in-the-middle slice will cause an argument.
Old-Fashioned Pineapple Upside Down Cake
Glossy caramel, pineapple rings and cherries over a soft, buttery sponge.
Ingredients
For the caramel top
- 60 g butter
- 100 g soft brown sugar
- 1 can (430 g) pineapple rings, drained & dried
- 8 glacé or maraschino cherries
For the sponge
- 175 g soft butter
- 175 g caster sugar
- 3 eggs, room temperature
- 175 g self-raising flour
- 1 tsp vanilla & 2 tbsp pineapple juice
Method
- Caramel layer. Oven to 180°C (fan 160°C / gas 4). Melt the butter, stir in the brown sugar, spread over the base of a deep 23 cm tin (not loose-based).
- Arrange the fruit. Pat the rings very dry, lay them over the caramel, cherry in the centre of each.
- Sponge. Cream the butter and sugar until pale. Eggs one at a time, then fold in the flour, vanilla and pineapple juice.
- Bake. Spoon the batter gently over the fruit, level, and bake 40–45 minutes until golden and a skewer comes out clean.
- The flip. Rest exactly 5 minutes. Knife round the edge, plate over the tin, one confident turn. Lift the tin away slowly — and take the applause.
Flip over the sink, not the table — the first time you do it, some caramel always makes a run for it.
Tips for a perfect turnout
Dry the rings
Pat them properly dry — wet fruit thins the caramel into syrup and soaks the sponge.
Five-minute flip
Not four, not ten. Five minutes rest, then flip — molten slides, set sticks.
Solid tin only
A loose-based tin leaks caramel all over the oven floor. Ask us how we know.
Questions, answered
Why did my cake stick to the tin?
Timing. Flip at 5 minutes — sooner and the caramel is molten and slides; later and it sets like glue. And never use a loose-based tin.
Can I use fresh pineapple?
Yes — thin rings or wedges, patted very dry. Canned in juice is the traditional and more reliable choice, though.
Why is the top soggy?
Wet fruit. Drain and pat the rings properly dry before they touch the caramel.