Prepare the pineapple

Cup of Yum
1. The first step is to slice off the top and bottom parts of the pineapple. Next, remove the peel, and carefully remove any large eyes on the pineapple as well.
2. Slice the pineapple into 1 inch thick slices. You do not have to remove the core.
3. Weigh the pineapple slices and make a note of the weight. This recipe is for 600 g of fresh pineapple. Calculate the weight of the sugar needed for this recipe by calculating 70% of the weight of the fresh pineapple. (If you want your syrup to be sweeter, you can use up to 100% sugar in terms of the pineapple weight.)

Grill the pineapples

1. Grill the pineapple over medium heat for about 1 - 2 minutes per side until each side is caramelized. You can either use an ourdoor bbq grill or indoor grill pan.
2. Place the grilled pineapple slices on a plate and let them cool down. The juices of the pineapple will collect at the bottom of the plate. DO NOT discard the juice.
3. When the pineapples have cooled down, cut the slices into smaller pieces. These pieces don’t have to be even-sized, but should be around 1 - 2 inches.

Mixing with the sugar

1. Add the pineapple pieces and juices into a large jug or wide-mouthed glass jar that is clean and dry.
2. Add the star anise and roughly ¾ of the sugar. Mix well with the pineapple.
3. Tamp down the pineapple so that it's nice and compact in the jar. Sprinkle the remaining sugar on top of this as evenly as possible. Cover the container with plastic wrap or a tight-fitting lid.
4. Let the fruit sit at room temperature for about 1 - 2 hours, and then transfer to the fridge. Keep it in the fridge for 24 hours (up to 48 hours). The sugar should be mostly dissolved by then.

Collecting the syrup

1. Place a large sieve over a bowl. Remove the pineapple syrup from the fridge. Check to see if all the sugar is dissolved. There might be some sugar settled at the bottom and that’s OK.
2. Gently coax out all the pineapple and dissolved sugar mixture onto the sieve. Be careful not to scrape out any undissolved sugar at the bottom when you do this.
3. Let the syrup collect into the bowl. Gently squeeze the pineapple pieces to draw out as much syrup / juice as possible. I also like to let the pineapple sit over the bowl for a little while, to let any syrup drain.
4. Once the syrup is collected in the bowl, remove the sieve with the pineapple pieces. You can discard the pineapple, or add it to muffins.
5. Pour the syrup back into the glass jar or jug with the undissolved sugar and stir the syrup until any remaining sugar fully dissolves.
6. Pass the syrup through a fine sieve to remove any pieces of fruit still left in the syrup.
7. Transfer the syrup into a bottle or container with an air-tight lid, and store in the fridge for up to 1 week.
8. The syrup will last up to 6 months in the freezer. Make sure to freeze in smaller portions, so that you can thaw out only what you need.