Dear Naseem,

You’re back!! I hope you had a great time watching Groundhog Day and hopping all over New York City.

It finally happened, I used those pineapple cake molds with the attempt to make pineapple cakes! About time since I’ve been dreaming about it since February.

Here’s how it went down: I saw pineapples on sale at the grocery store and bought them. I pretended that I knew how to pick the ripe ones because they were all smelling so good. Went home to wash the metal molds again because I couldn’t remember if I cleaned them when they were gifted to me. Then I rolled up my sleeves to get to work.

Pineapple Cookies
Recipe adapted from Sweet
Makes 40 small rectangular tarts and excess pineapple filling

Pineapple Filling
2 pineapples
1¾ granulated sugar
1 teaspoon vanilla extract
6 whole star anise

Shortcrust Pastry
2⅓ cups all-purpose flour
¾ cup confectioners’ sugar
¼ teaspoon salt
¾ cup unsalted butter
Zest from 1 lemon
1 large egg yolk
4 teaspoon water

Pineapple Filling:

1. Peel, core, and chop the pineapple flesh into 2-inch cubes
2. Place the cubed pineapples in a food processor and pulse until it becomes a purée.
3. Pour the purée over a sieve to let our the excess juice. Save the juice to mix with a can of ginger ale – it makes for a great drink while you work!
4. Place the pineapple purée in a large saucepan and add in the sugar, vanilla extract, and star anise. Turn the stove up to medium-low heat and stir until the sugar dissolves. Increase the heat to medium and stir every 3-5 minutes to avoid burning.
5. Depending on the remaining juice content and heat of your stove, this can take up to 30-40 minutes before the purée starts to thicken and turn a golden colour. You’re not making a jam, so you have to keep cooking until the filling holds it shape when spooned.
6. When it’s ready, turn off the heat and remove it from the stove top. Let it cool for about half an hour before transferring to an airtight container. Keep this in the fridge until you’re ready to assemble the tarts.

Shortcrust Pastry:

1. Using the food processor again, sift in the flour, confectioners’ sugar, and salt. Cut the cold butter into small cubes and add it in with the lemon zest. Pulse to mix in. Whisk the egg yolk and water together, add it to the mixture and pulse until the dough comes together.
2. Take the dough out wrap it tightly in plastic wrap. Let it chill in the fridge for an hour. Take out the dough half an hour before you’re ready to assemble.

Pineapple Cookies:

1. Brush the molds with melted unsalted butter.
2. Preheat the oven to 400°F.
3. Scoop the pineapple filling into a piping bag, set aside.
4. Lightly dust your working surface with flour and roll out the pastry dough. Using the mold, stamp out the shapes and layer it on the bottom of each mold.
5. Pipe a dollop of pineapple filling onto the center of each rectangle.
6. Using the leftover pastry dough, repeat by stamping out the shape of the mold. Each sheet will be placed on top of the pineapple filling. Tuck in the sides as best you can so that it seals the filling in.
7. Bake for 20 minutes or until the pastry is golden brown. Remove from the oven and let it cool before transferring it to a wire rack. Use a tong to pop the tarts out of the metal molds.

I somehow managed to get Howard to peel, core, and chop all the pineapple for me. I stood around waiting and snapped photos. There’s also something very satisfying about seeing a solid fruit get puréed into a beautiful sauce.

At this point, I did wonder if I should just pour this pineapple purée over some ice cream. Or look up a recipe for Dole Whip. But I soldiered on with the original plan.

Here’s the golden colour of the pineapple purée cooked for over half an hour. Wear comfy slippers or have a squishy kitchen mat while you stir this filling past the consistency of jam.

Alright, the filling is cooling in the fridge. Time to butter those molds so that the cookies pop right out.

I used one of the molds to cut out 40 rectangles and a bench scraper to help pick them up.

Here goes the bottom layer.

I used a piping bag since it would be easier to distribute each pineapple dollop onto the bottom layer of pastry.

I was pretty conservative as I didn’t want any to leak out – but of course, some did manage to escape after it was baked.

Okay, this again. Another 40 rectangles for the top layer.

I placed those gently on top and pushed down around the edges to seal the pineapple filling in.

When they were ready, I had them cool for a bit and used a tong to pop the cookies out of the hot metal molds. Then ate one while it was still hot – probably tasted the best then because who doesn’t love hot pockets?

They kind of look like Fig Newtons?

But after various taste-testers, I think the conclusion is that these aren’t pineapple cakes (my heart breaks), but they are amazing pineapple-filled cookies (my heart has hope again).

I think my least favourite part of this recipe is washing the molds after. Luckily, I only had to give them a quick scrub as they survived the dishwasher (just taking risks here and there).

I liked the filling but I’ll just have to find a different dough recipe for a more cake texture. I know we discussed maybe adding baking powder or baking soda? Although when you mentioned winter melon, I am intrigued on how to make the filling.

Also, this made a ton of filling, I could probably cut the recipe in half. Or enjoy the additional pineapple tart I would have to make each time.

Sincerely,
Syl