Preheat oven to 325°F. Wrap the outside of a 9-inch springform pan in a double layer of heavy-duty foil. Coat inside of pan with baking spray.

Stir together cookie crumbs, butter, 2 tablespoons sugar, and ½ teaspoon cinnamon in a medium bowl until well combined. Press into bottom of prepared pan. Bake until edges are lightly golden, 20 to 25 minutes. Let cool on a wire rack 30 minutes.

Meanwhile, beat cream cheese with a stand mixer fitted with a paddle attachment on medium speed until smooth, about 2 minutes. Add pudding mix, sour cream, flour, vanilla, coconut extract, 1 cup sugar, and ¾ teaspoon cinnamon; beat on low speed just until combined, about 1 minute. Add eggs, 1 at a time, beating until just combined after each addition, about 1 minute. Stir in crushed pineapple with juice until combined.

Spread batter over prepared crust. Place springform pan in a large roasting pan; carefully pour boiling water into roasting pan, filling halfway up sides of springform pan. Bake until top appears dry and edges are set, 1 hour, 20 minutes to 1 hour, 25 minutes. Turn off oven, and prop open door; let cheesecake cool in oven 1 hour.

Remove cheesecake from oven; remove and discard foil. Gently run a knife around outer edges of cheesecake to loosen from pan; let cool at room temperature 1 hour. Chill, uncovered, until completely cooled and set, at least 8 hours or up to 24 hours.

Remove sides of springform pan; transfer cheesecake to a plate. Garnish with pecans, coconut flakes, and dried pineapple rings.