In a large mixing bowl combine sugar, butter, milk and almond extract. Mix until combined. Knead into a large ball.: The scent will be sweet and nutty, the texture turning from powdery to a supple dough under your fingers, which should be cool and slightly tacky but not wet. This transformation matters because a uniform dough keeps centers consistent, and kneading develops cohesion so they do not fall apart during wrapping. A common mistake is adding too much milk which makes the mixture sticky, so add it slowly and use your palms to press the dough together, folding rather than overworking it. If it feels greasy the butter may be too soft; chill briefly.
Roll into 1 inch balls and flatten into a 2 inch circle. Place cherry on top and wrap around cherries and tightly roll in hands.: You will feel the cool firmness of the maraschino cherries as you place them, and the dough should stretch evenly to enclose each fruit. Wrapping tightly is crucial to prevent gaps where syrup can leak and to maintain shape while dipping. Watch for thin spots which tear easily, and if one appears, press edges together and roll gently to seal. Rushing this step leads to uneven centers that leak during storage.
Place covered cherries on waxed lined baking sheet with stems pointing up.: The cherries will glisten as you set them down, and arranging with stems up keeps the points of contact minimal so the coating sets cleanly. This orientation also makes dipping easier later. Avoid crowding the sheet because touching pieces can mar the coating. If they slump, chill the tray briefly to firm the centers before proceeding.
Cover loosely and refrigerate 4 hours or overnight.: Cooling firms the centers and helps the dough and cherry bond, producing a nice contrast when dipped. The aroma in the fridge will be faintly sweet, and chilling prevents the centers from falling apart when they meet warm chocolate. A mistake here is skipping the chill, which often results in misshapen candies; if time is short, refrigerate for at least several hours to set the centers.
Melt the almond bark and shortening in microwave according to package directions.: As the chocolate almond bark warms, it will become glossy and fluid, releasing a comforting chocolate scent. Stir between microwave bursts to avoid overheating, because burnt chocolate becomes grainy and will not reset properly. The shortening smooths and thins the melt, improving flow for dipping and giving a shinier finish. Overheating is the main pitfall, so use short intervals and stir until uniformly melted.
Holding on to stem, dip cherries into chocolate, set on waxed paper to harden. Store in a covered container at room temperature. To get the gooey center we recommend them sitting for 2-4 weeks.: When you dip, the sound of the chocolate coating is quiet and viscous, and you should see it cling and then level into a smooth shell. The stem gives you control, letting excess chocolate drip off before you place the cherry down. A glossy, even shell indicates proper temperature and consistency; if the chocolate looks dull or streaky, it may have seized or cooled too much. If that happens, gently rewarm and stir to smooth it before continuing.
Store in a covered container at room temperature. To get the gooey center we recommend them sitting for 2 to 4 weeks: Over days the center softens and becomes almost caramel like, and the chocolate remains pleasantly firm. Store stacked in a single layer or separated with paper so they do not stick. Humidity and heat are the enemies here, so avoid warm locations. A common error is refrigerating after chocolate sets which can introduce condensation; room temperature storage in a cool cupboard is ideal for maintaining texture.
