These raisin pie cookies are amazing — the filling is ooey gooey, almost candy-like and the cookie is a chewy, soft brown sugar cookie reminiscent of shortbread.
These cookies remind me of the flavor of the Canadian classic – buttertarts! They’re exceptional and go great with a cup of tea!

I must say that the first attempt of the cookies were a complete fail, as you will see. I tried baking the same dough again after it was chilled, which was just as much a flop as the first. So I changed up the dough, and now the cookies turned out great. I share the dough that actually works with you below!
Let’s get started!
Attempt 1 – Fail!
Cream butter and sugar together until well combined.

Add vanilla and milk. Stir.

Add flour, baking powder and salt. Mix well.


Roll into balls. I scooped the cookie dough and placed them all on a cookie sheet.

Place parchment paper on baking sheet. Place cookies on sheet. Make indents in cookies.

For the filling, mix sugar and butter together. Add corn syrup and vanilla and stir until creamy. Stir in raisins.



Spoon into cookies being careful to not over fill.

Bake at 350F for 8 to 12 minutes or until cookie is golden around edges and filling is set.
My first batch of as a bit of a cookie fail!

So, I refrigerated the cookies overnight and this is how they turned out. Haha, a bit better, but not really. Luckily they taste amazing and almost butterscotchy-candy-like!

I cooked the last of this dough up the next day, and oddly, the cookies somewhat kept their shape.

I changed up the recipe a bit, adjusted it and let’s try again!
Attempt 2 – Success!
Cream butter and sugar together until well combined. Add vanilla and milk. Stir. Add flour, baking powder and salt. Mix well. Roll into balls. Place parchment paper on baking sheet. Place cookies on sheet and make indents in cookies.









Next time, I’d add the raisins to the cookie and drizzle the cookies with a brown sugar frosting. I think that would be a lovely variation!
12 Days of Cookies… Day 7 — Raisin Pie Cookies
Cookie
1/2 cup butter
1 cup dark brown sugar
1 tbsp milk
1 tsp vanilla
2 eggs
2 cups flour
1/2 tsp baking soda
1 tsp baking powder
1/4 tsp salt
Raisin Pie Topping — this is enough for 2 batches of cookies
2/3 cup raisins
1/2 cup corn syrup
1/4 cup brown sugar
2 tbsp butter
1 tsp vanilla
Cream butter and sugar together until well combined. Add vanilla and milk. Stir. Add flour, baking powder and salt. Mix well. Roll into balls. Place parchment paper on baking sheet. Place cookies on sheet and make indents in cookies.
For the filling, mix sugar and butter together. Add corn syrup and vanilla and stir until creamy. Stir in raisins. Spoon into cookies being careful to not over fill.
Bake at 350F for 8 to 12 minutes or until cookie is golden around edges and filling is set.
enjoy from Our City Homestead to yours