Preheat oven to 375 degrees Fahrenheit.: You should sense the kitchen warming as the oven reaches 375 degrees Fahrenheit , and preheating ensures even baking so cookies spread and set predictably. A properly preheated oven gives a slight whoosh when you open it, and the top rack heat will help the edges turn a pale golden that signals doneness. If you skip preheating, cookies can bake unevenly and end up too pale or dense. Common mistake to avoid, placing the tray in before the oven is at temperature, can result in a longer bake and drier cookies.
In a large bowl mix together butter, powdered sugar and vanilla until blended.: As you cream the softened butter with the powdered sugar and vanilla , pay attention to texture, it should become smooth, pale, and slightly fluffy, releasing a rich, milky aroma. The creaming traps tiny air pockets that help with tenderness, and the powdered sugar dissolves into the butter to prevent grittiness. If the mixture looks oily or separated, your butter was too warm, so chill briefly and rework. A frequent pitfall is under beating, which can yield a dense, compact cookie rather than a delicate one.
In a separate bowl combine flour, salt and ground almonds. Combine dry mixture with butter mixture.: You will notice a nutty scent as the ground almonds meet the flour and salt . Sifting or whisking these dry items helps distribute the salt and breaks up any lumps in the ground almonds . Folding the dry mix into the creamed base should be done gently until just combined, stopping when you see no streaks of dry flour . Overmixing develops gluten and leads to a tougher bite, so fold with care. If your dough feels crumbly, pressing it should bring it together; if it becomes greasy, you likely used too warm butter .
With about 1 tablespoon of dough, make a pit in the middle and place a cherry half in the pit then fold dough over the cherry to form a ball. Place on parchment paper lined baking sheet. Flatten cookie dough slightly.: When you shape each ball the dough should feel cool and slightly tacky, and the little pit helps cradle the maraschino cherry so it stays centered. Press gently to enclose the cherry, the dough should seal without tearing, and when placed on the parchment it will hold its shape. Flattening slightly helps the cookies bake evenly and exposes more surface for the glaze to cling to. Avoid over handling as the warmth of your hands can soften the dough too much, making the cookies spread excessively during baking.
Bake at 375 degrees Fahrenheit for 8-9 minutes or until edges are just starting to turn golden brown. Remove from oven and cool on a wire rack.: In the oven you will see the tops set and the edges take on a faint golden blush, that is your cue to remove them. The cookies continue to firm as they cool, so pull them when the centers are still slightly soft to the touch. Placing them on a wire rack prevents steam from making the bottoms soggy and helps the texture remain crisp at the edges. A common error is leaving them too long, which dries them out, or removing them too soon, which causes them to collapse while cooling.
In a small bowl mix together powdered sugar, cherry juice and almond extract. Add enough milk to make it dipping consistency. Dip tops of cookies in icing, flip over and place on wire rack. Sprinkle with red sugar.: The glaze should smell faintly of cherry and almond , and have a glossy, slightly thick texture so it coats the cookie without dripping off. When you dip the tops, the glaze will cling and set into a smooth sheen; flipping them over onto the wire rack allows excess to drip away. While the glaze is still tacky, the red decorating sugar will adhere and sparkle. A trouble to watch for is overly thin glaze, which will run and pool; if this happens, thicken with more powdered sugar to maintain a nice coating.