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Scrape seeds from vanilla bean into a small food processor. Add 1/2 cup sugar and anise seeds; cover and pulse several times to combine.
In a large mixing bowl, beat butter with an electric mixer on medium to high speed for 30 seconds. Add sugar-anise mixture. Beat until fluffy, scraping side of bowl occasionally. Beat in flour and salt until combined. Divide dough in half. Cover and chill about 1 hour or until dough is easy to handle.
Meanwhile, combine cinnamon and the remaining 1 tablespoon sugar in a small bowl.
Preheat oven to 275°F. On a lightly floured surface, roll half the dough at a time to 1/2-inch thickness. Using a 2- to 2 1/2-inch diamond shaped cookie cutter, cut out dough. Place cutouts 1 inch apart on an ungreased cookie sheet. Bake for 35 to 40 minutes or until edges are firm to the touch. Cool on cookie sheet 2 minutes. Transfer cookies to a wire rack; sprinkle with cinnamon-sugar mixture and let cool.