Start by placing the pitted dates in a saucepan with 1 cup of water. Bring to a gentle boil over medium heat, then reduce the heat and let it simmer for about 5-7 minutes, or until the dates are soft and have absorbed most of the water. Stir in the vanilla extract, then remove from heat and let it cool slightly.
Preheat your oven to 350°F (175°C). Line your 9x9 inch baking pan with parchment paper, leaving some overhang to make it easier to lift out the squares later.
In a large mixing bowl, whisk together the rolled oats, all-purpose flour, brown sugar, baking soda, salt, and cinnamon until thoroughly combined.
Add the cold cubed butter to the dry mixture. Using a knife or pastry cutter, cut the butter into the mixture until it resembles coarse crumbs. It’s okay if some small chunks of butter remain; they will create a flakier texture.
Take the cooled date mixture and fold it into the dry ingredients using a rubber spatula. Mix until just combined; do not overmix.
Spread the mixture evenly into the prepared baking pan, pressing it down firmly. Bake in the preheated oven for 25-30 minutes, or until the edges are golden brown.
Once baked, remove from the oven and let the date squares cool in the pan for about 10 minutes. Then, lift them out using the parchment overhang and transfer to a wire rack to cool completely before cutting into squares.
