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Step 1
Chop or grind the raisins.
Step 2
In a saucepan, mix the brown sugar and flour. Add the water and raisins.
Step 3
Bring to a full rolling boil over medium heat, whisking occasionally.
Step 4
Remove from the heat and cool.
Step 5
Cream the shortening and sugars and beat until fluffy.
Step 6
Add the eggs and vanilla and mix well.
Step 7
Combine the dry ingredients and add to the creamed mixture alternately with the milk.
Step 8
The dough is very soft. And if you feel like it's too sticky to handle, you can add another 1/4 - 1/2 cup of flour or refrigerate it for a bit.
Step 9
Preheat the oven to 350°.
Step 10
Sprinkle a layer of flour onto your clean countertop. Place half of the dough onto the flour. Sprinkle the top with a dusting of flour and roll it out, with a rolling pin, to about 1/8 - 1/4 inch thick. If the dough wants to stick to the counter, lift up the edges and add more flour.
Step 11
Use a round cookie cutter or cup to cut out circles of dough. (I used my 2 1/4-inch cutter, but you can make them smaller or bigger according to how big you want your cookies).
Step 12
Place the dough circles, at least an inch apart, onto a parchment-lined cookie sheet.
Step 13
Put a heaping teaspoon of raisin filling onto the top of each circle. (You will need to adjust the amount according to the size of your cookies. I used a heaping teaspoonful for 2 1/4" cookies.)
Step 14
Roll out the remaining dough and cut more circles of the same size. Using a thimble or tiny round object, cut a small hole in the center of each circle for the top. (Dip the thimble in flour to prevent the dough from sticking.)
Step 15
Place the top circle over the raisin filling and lightly press the edges together.
Step 16
Use all the scraps/remaining dough and roll it out to make more cookies until no more dough is left.
Step 17
Bake the cookies at 350° for about 10 minutes or until the bottom edges are lightly browned.
Step 18
Let them rest on the tray for a moment, then transfer them to a wire rack to cool.
Step 19
Store in an airtight container. And I recommend freezing any cookies that won't get eaten within three days, to keep them fresh.