In the bowl of a stand mixer fitted with the paddle attachment, beat butter and brown sugar at medium speed until fluffy, 3 to 4 minutes, stopping to scrape sides of bowl. Add eggs, one at a time, beating well after each addition. Beat in extracts.
In a medium bowl, whisk together flour, baking powder, and salt. With mixer on low speed, add flour mixture to butter mixture alternately with buttermilk and amaretto, beginning and ending with flour mixture, beating just until combined. Fold in Amaretto Drunken Cherries and chocolate.
Spray a 10-cup Bundt pan with baking spray with flour. Spoon batter into prepared pan. Forcefully tap pan on kitchen towel-lined counter several times to settle batter and release any air bubbles.
Bake until a wooden pick inserted near center comes out clean or an instant-read thermometer registers 200°F (93°C), 1 hour to 1 hour and 10 minutes. Let cool in pan for 15 minutes. Invert cake onto a wire rack, and let cool completely.
Place cake on cake plate. Using a spoon, drizzle Cherry Amaretto Glaze into and over grooves of cake. Garnish with fresh cherries, if desired.
Recipe by Bake from Scratch at https://staging.bakefromscratch.com/cherry-chocolate-amaretto-bundt/