2 tablespoons unsalted butter
1/2 cup plus 2 tablespoons packed light brown sugar
1 1/4 cups whole milk
3/4 cup heavy whipping cream
5 large egg yolks
1/2 teaspoon kosher salt
1 teaspoon vanilla extract
11 tablespoons unsalted butter, softened
1/4 cup granulated sugar
1 large egg, at room temperature
1/4 cup sorghum molasses
1 3/4 cups whole-grain gluten-free flour blend
1 1/8 teaspoons baking soda
3/4 teaspoon ground cinnamon
1/2 teaspoon ground chia seed
1/2 teaspoon ground ginger
1/2 teaspoon kosher salt
1/4 teaspoon freshly grated nutmeg
Turbinado or other coarse sugar, for coating
1/2 small pineapple, peeled, cored and cut in 1/2-inch dice
2 tablespoons packed light brown sugar
2 teaspoons dark rum
1 teaspoon vanilla extract
Pinch kosher salt
2 teaspoons unsalted butter
Caramel sauce, for serving
Edible flowers, for serving
Powdered sugar, for serving
For the butterscotch ice cream base: Combine the butter and 5 tablespoons brown sugar in a medium saucepan over medium heat. Cook, stirring frequently with a heatproof rubber spatula, until the mixture is thick and bubbly and darkens slightly in color. Carefully and slowly, pour in the milk and cream. Increase the heat to medium-high and cook, stirring occasionally, until the caramel is dissolved and the mixture is scalding hot. Turn off the heat.
Whisk together the egg yolks, salt and remaining 5 tablespoons brown sugar in a bowl until well combined. Slowly ladle in about one-third of the hot milk mixture, whisking constantly. Pour the tempered yolk mixture back into the saucepan. Reduce the heat to medium-low and heat slowly, stirring constantly with a rubber spatula or wooden spoon, until the custard reaches 175 degrees F and has thickened slightly. Do not allow to boil or the mixture will curdle. Set the pan into a larger container half-filled with ice and water and stir occasionally until completely chilled. Stir in the vanilla extract. If the custard is not totally smooth, strain through a fine-mesh strainer or blend until smooth with a handheld immersion blender.
Process in an ice cream machine according to the manufacturer's directions. Store in the freezer until firm, at least 4 hours.
For the sorghum molasses cookies: Add the butter and granulated sugar to the bowl of a stand mixer (or a large bowl, if using a handheld mixer). Using the paddle attachment (for the stand mixer), beat on medium speed until light and fluffy, about 3 minutes. Scrape the sides and bottom of the bowl with a rubber spatula, and beat again for 20 seconds to ensure a homogeneous mixture. Add the egg and beat until incorporated. Add the molasses and beat again until incorporated. Scrape the sides and bottom of the bowl with a rubber spatula, and beat again for 20 seconds.
Combine the flour blend, baking soda, cinnamon, chia seed, ginger, salt and nutmeg in a medium bowl with a whisk. Add the dry mixture to the stand mixer bowl and stir on low speed until the dry ingredients are moistened. Increase the speed to medium and beat until smooth, about 1 minute. Scrape the sides and bottom of the bowl with a rubber spatula, and beat again for 20 seconds. (For easier shaping, chill the dough for several hours until firm.)
Preheat the oven to 350 degrees F (if using a convection oven, preheat to 325 degrees F.) Line 2 baking sheets with parchment. Using a small ice cream scoop, shape 1-ounce balls of dough (2 tablespoons in size) and roll them lightly in turbinado sugar. Place on the prepared baking sheets 4 inches apart and flatten slightly with your hands to a 1/2-inch thickness.
Bake, rotating the pans once from front to back and from the bottom rack to the top rack during baking, until rich golden brown all over and puffed in the center, about 18 minutes. They will spread quite a bit and feel just set. Allow to cool completely, then freeze until ready to assemble the sandwiches.
To assemble the sandwiches: Remove the ice cream from the freezer. If it is too firm to scoop easily, allow to soften for 5 to 10 minutes.
Remove the cookies from the freezer. Place 6 cookies face-down on a baking sheet. Top each cookie with a generous scoop of butterscotch ice cream, then top each with another cookie, face-up. Press down gently with the palm of your hand until the ice cream spreads to the edges of cookies. Place the sandwiches in the freezer until ready to serve.
For the pineapple: Toss the pineapple with the brown sugar, rum, vanilla and salt in a medium bowl. Let marinate, stirring once or twice, until the sugar has dissolved and the pineapple releases its juices, 20 to 30 minutes. Drain the pineapple, reserving the marinade.
Heat a large cast-iron skillet over medium heat. When the pan is quite hot, add the butter and swirl to coat the bottom of the pan. Add the pineapple to the pan, spreading the pieces out in a single layer and taking care not to crowd the pan. When the pan has recovered its heat, pour in the marinade and allow to reduce until thickened and bubbly. Turn over the pineapple pieces and cook, stirring occasionally, until the liquid is all but evaporated and the pineapple is nicely browned all over. Remove the pineapple from the skillet.
To serve: Cut each ice cream sandwich in half and plate with the warm, caramelized pineapple. Add a drizzle of caramel sauce and garnish with a bright edible flower and a sprinkle of powdered sugar. Enjoy!
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