Start the filling first since it needs time to cook down and cool completely before assembling. Pour the crushed pineapple with its juice into a medium saucepan, then add 1 cup sugar, 1/2 cup water, lime zest, and lime juice. Bring the mixture to a boil over medium-high heat, then reduce to a simmer and cook for about 50 minutes, stirring occasionally, until the mixture thickens and reduces significantly. Once thickened, carefully blend the filling until smooth using an immersion blender or transfer to a food processor—work in batches if needed. Return the blended filling to the pan and cook for another 5 minutes while stirring constantly until it reaches a deep amber color and becomes very thick. Pour the filling onto a plate to cool completely; this usually takes 30-45 minutes while you prepare the cookie dough.

While the filling simmers, prepare your dry ingredients. Finely chop the pecan halves—I like to pulse them in a food processor just until they're broken into small pieces but not powdery, as this makes them easier to fold into the dough without creating texture clumps. In a medium bowl, whisk together the chopped pecans, flour, baking soda, and kosher salt until evenly distributed. Set this dry mixture aside.

In a large bowl, beat the softened butter and 3/4 cup sugar together for 2-3 minutes until the mixture is light, fluffy, and noticeably pale in color—this aerates the dough for better texture. Add the egg yolks and vanilla extract and beat well until fully incorporated, about 1 minute. Gradually add the dry ingredient mixture from Step 2 to the wet mixture, stirring gently with a spatula or wooden spoon until just combined. Don't overmix once the dry ingredients are added, as this can develop too much gluten and make the cookies tough. Divide the dough in half and shape each portion into a flat disk, then wrap tightly in plastic wrap and refrigerate for at least 2 hours—I often prepare this step while the filling cools, so the timing works perfectly.

About 15 minutes before you're ready to bake, preheat your oven to 350°F (175°C). Remove one dough disk from the refrigerator and let it soften at room temperature for 5-10 minutes—this makes rolling easier without the dough cracking. The dough should be pliable but still cool. Line two large baking sheets with parchment paper.

Roll the softened dough disk between two sheets of parchment paper to an even 1/4-inch thickness. Using your favorite cookie cutter (a round cutter works well for linzer cookies), cut an equal number of bottom and top pieces—for example, if you cut 12 bottoms, cut 12 tops. From the top pieces only, use a smaller cutter (about 1 inch) to cut out the center shape, creating a window. Place all cookie pieces on the prepared baking sheets, spacing them about 1 inch apart. Bake for about 9 minutes until the cookies are just set and lightly golden at the edges. Transfer the warm cookies to a wire rack to cool completely, then repeat this entire step with the second dough disk.

Once all cookies are completely cooled and the pineapple filling from Step 1 is fully set, it's time to assemble. Spread about 1 teaspoon of the pineapple filling onto each solid bottom cookie, being careful not to overfill. Dust the top cookies (the ones with the cutout window) generously with powdered or decorative sugar so you can see the filling through the opening. Gently press each sugared top cookie onto its corresponding filled bottom cookie, creating a sandwich with the filling showing through the window. Allow the assembled cookies to set for 10-15 minutes before serving or storing.