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Drain, rinse, and dry the cherries by pouring them into a colander and placing them on paper towels to dry. Use a salad spinner to speed up the process if available.
Mix the butter, corn syrup, and almond extract together until smooth.
Stir in the sugar, 1 cup at a time, adjusting the amount as needed for desired consistency. Knead the last ½ cup to cup by hand until soft but not sticky.
Using about a teaspoon of sugar dough for each cherry, roll and flatten the dough, place the cherry in the center, and mold the dough around the cherry.
Place the coated cherries on parchment paper and freeze overnight, or for at least an hour.
While cherries are chilling, melt the chocolate chips with shortening in a glass bowl over simmering water on the stove.
Dip each coated cherry into the melted chocolate using a dipping scoop, shake off excess chocolate, and place on parchment paper until hardened. Transfer each cherry to a mini baking cup.
Store in an airtight container. For best results, make about a week or two before giving out.