Using an electric mixer, mix together the shortening, granulated sugar, egg and vanilla.
Blend in the flour mixture alternately with the milk, beginning and ending with flour. Set aside.
Spray each mason jar with cooking oil like Pam. Place 1 cherry on the bottom of each jar. Place 1 tbs of crushed pineapple on top of each cherry.
Pour batter into each jar only filling about half way.
Place all jars on a cookie sheet and bake for 15-20 minutes or until golden brown on top.
Remove from oven and let cool for about 10 minutes. Serve right in the jar or tip upside down to remove cake.
Place seal tight lids on top and store in the fridge for up to 1 week. Enjoy!
Notes
To add to the traditional pineapple upside down cake taste, add a teaspoon of brown sugar into the bottom of each mason jar, on top of the cherry. It'll give the cake a syrupy topping once you tip it out. Enjoy!