Prep & make the pineapple syrup: Strain the crushed pineapple and remove as much liquid as possible. Really squeeze the liquid out. Set aside.
Add 1 1/2 cups of pineapple juice to a medium saucepan over medium-high heat. Bring to a boil and reduce until you have a 1/4 cup of pineapple juice left (it will be kind of thick and sticky). This can take about 40 minutes. Set aside to cool completely.
Preheat the oven to 350 degrees F and make sure a rack is in the center position, as well as one on the bottom (which will hold a pan with boiling water to create steam). Grease a 9-inch round springform or loose-bottom baking pan and set aside.
Make the crust: Add the flour, sugar, macadamia nuts, cinnamon, and salt to the bowl of a food processor. Pulse until the nuts are finely chopped.
Add the cold diced butter to the food processor. Pulse to cut the butter into the flour mixture, stopping as soon as the butter is broken into tiny pieces and coated in flour—the mixture will sort of look like clumpy sand. Somewhere around 25 to 30 quick pulses should do it, you don't want to overmix or you'll get tough, greasy shortbread. It's okay if it seems a little dry.
Transfer the macadamia nut shortbread dough to your prepared pan. Spread into an even layer, then press the crumbs down to form the crust. I used the bottom of a glass. it’s easiest to start around the sides and work your way towards the center.
Bake the crust for 18-22 minutes, just until the edges are slightly browned (the color does not change too much, so be careful not to overbake). Remove from the oven and set aside to cool completely for assembly.
Make the filling: Add room temperature cream cheese and sugar to the bowl of a stand mixer fitted with the paddle attachment. Beat them on low speed until super smooth.
Then add the vanilla extract and eggs, one at a time, allowing each egg to become fully incorporated prior to adding the next.
In a small bowl, whisk together the pineapple juice concentrate, sour cream, salt, and cornstarch until smooth, then stir in the crushed pineapple.
Add to this mixture to your cream cheese in the stand mixer. Mix on low speed (you don't want to whip air into it) until *just* combined. Scrape down the sides of the bowl and mix for another 20 seconds on low.
Assemble & bake: Pour half of the cheesecake filling into the cooled shortbread crust. Scatter pineapple chunks over the filling, then cover with the remainder of the batter.
Bake at 325°F (160°C) for 50–60 minutes, until edges are set and the center is slightly jiggly (I prefer mine very slightly under, vs. overbaked). Once it's done, turn off the oven and crack the oven door. Let the cheesecake sit for one hour in the oven as it cools.
CHILL! Remove from the oven and let it sit at room temperature for 30 minutes, then place into the refrigerator for at least 4 hours (overnight is fine too).
If desired, you can amp up the pineapple flavor with a pineapple whipped cream (cream, powdered sugar, pineapple juice), or a pineapple curd or compote. I'm definitely going to try one of the latter next time I make this!