• Prep times are same for both cookies and jam, cooking time for jam is one hour, baking time for cookies is 9 minutes. The extra time is for chilling the jam overnight.

Make the jam a day before making the cookies:

• Add all but rum to a saucepan, bring to a boil, lower heat to a simmer and simmer for 45 minutes. Strain all but 2 tablespoon of the excess liquid ( keep liquid for cocktail syrup) and place the pineapple plus 2 tablespoon liquid in a food processor or blender and blend until almost smooth. Can still be chunky. Transfer to an airtight jar and chill overnight to set. Bring to room temperature before using in the cookies.

For the Cookies:

• Heat oven to 375 Deg F. Line baking sheets with parchment paper.
• In a stand mixer, or large bowl and using a hand mixer, cream together the butter, sugar, vanilla and egg yolk until light and fluffy. Mix together the flour, cornstarch and salt. Add to the butter mixture and mix until combined. This is a soft dough. Don’t over mix, since you will be rolling the dough into balls and don’t want to make the cookies too tough. 
• Roll the dough into 1” balls ( ½oz/15g). Indent the middle by ½ an inch with thumb or back of a ½ teaspoon. Fill with a scant teaspoon of the 5 spice pineapple jam. Work with one cookie at a time, you want to fill with jam as soon as you make the indent. Place cookies two inches apart on a parchment lined baking sheet. 
• Bake at 375 on a flat light aluminum baking sheet with a piece of parchment paper on it for 8-10 minutes
• Cool cookies on baking sheet for a few min then carefully transfer to wire cooling rack to cool completely.
• Optional - you can dust with powdered sugar if you like.