Aunt Clara's Filled Molasses Cookies

Preheat the oven to 375 degrees F (190 degrees C).

In a saucepan, toss raisins with 1 teaspoon flour until coated. Stir in 1/4 cup sugar, 1 teaspoon vanilla extract, and lemon juice. Pour 1 cup boiling water over the raisin mixture; bring to a boil. Cook, stirring constantly, until raisins start to break down and the mixture thickens (5-10 minutes). Remove from heat; cool to room temperature.

In a bowl, combine 2 3/4 cups flour, 3/4 cup sugar, and salt; set aside.

In a separate large bowl, whisk melted shortening and molasses together; stir in 1 teaspoon vanilla extract. In a heatproof measuring cup, dissolve baking soda in 1/3 cup boiling water; stir into the molasses mixture until it foams and is well combined. Stir the flour mixture into the molasses mixture until a stiff dough forms.

Divide the dough in half; shape each into a ball. Cover one dough ball with a damp paper towel. Roll out the remaining dough ball until 1/8-inch thick; cut into rounds using a round cookie cutter or the top of a glass. Place bottom cookie rounds 2 inches apart on a baking sheet; top each with 1 tablespoon of raisin filling.

Roll out the remaining dough ball until 1/8-inch thick; cut into rounds using the same cutter. Moisten fingers slightly with water; carefully press top cookie rounds from the centers outwards until each is about 1/4-inch larger than the bottom rounds on the baking sheet. Working from one edge, place one top round over one bottom round and filling; press firmly to enclose the filling and seal the cookie. Lightly press the tops of the cookies to settle the filling in the pockets.

Bake in the preheated oven until the cookie is set (10-12 minutes). Cool briefly on the baking sheet before transferring to a wire rack to cool completely.