Position racks in the upper and lower thirds of the oven and preheat to 350 degrees F. Spread the almonds on a rimmed baking sheet and bake until slightly darkened, about 10 minutes; let cool completely. Transfer to a food processor and pulse until finely ground. Add the flour and pulse to combine.
Beat the butter in a large bowl with a mixer on medium-high speed until light and fluffy, 3 to 5 minutes. Add 1/2 cup confectioners' sugar, the vanilla and almond extracts, and salt and beat until combined. Reduce the mixer speed to low; add the flour mixture and beat until just incorporated. Cover and refrigerate until slightly firm, about 30 minutes.
Meanwhile, combine the dried cherries, amaretto and 1 tablespoon water in a small microwave-safe bowl and microwave 30 seconds; set aside until the cherries are plump, about 20 minutes.
Scoop out a tablespoonful of dough, press a dried cherry into the center, then shape the dough into a ball, enclosing the cherry. Repeat with the remaining dough and cherries and arrange about 1 inch apart on 2 ungreased baking sheets. Bake, switching the position of the pans halfway through, until lightly golden on the bottom, 15 to 20 minutes. Put the remaining 1 cup confectioners' sugar in a large shallow bowl. Let the cookies cool 5 minutes on the baking sheets, then carefully transfer to the bowl with the sugar and gently toss. Transfer to racks to cool completely, then toss in the sugar again.
Photograph by Johnny Miller
Courtesy of Food Network Magazine