Preheat oven to 325 degrees F. Line lightly colored baking sheets with parchment paper and set aside. In the bowl of a stand mixer, add your butter, granulated sugar, powdered sugar, canola oil, water and egg. Stir on low with the paddle attachment to slowly incorporate, then increase speed to medium high until thick, light and fluffy. (Should take 30 seconds to 1 minute.) Scrape the sides and mix again briefly.
Add in the remaining dry ingredients and stir until just incorporated. Scrape the sides and especially the bottom of the bowl to ensure the cookie dough is coming together as it should. Stir again briefly.
Using a large cookie scoop (3 tablespoon scoop) scoop level cookie dough balls onto a parchment paper lined baking sheet, 6 per sheet. Using a heavy bottomed glass approximately 2 1/2 inches in diameter, dip the bottom of the glass into flour and then gently flatten the dough balls so they are 1/2-2/3 inch thick. Bake 11-12 minutes in preheated oven. Cookies should look matte and slightly puffed without any brown edges. Centers will be soft with edges cooked.
Cool on baking sheet 5 minutes before transferring to cooling rack. I like to lift the entire sheet of parchment paper with the cookies still on it and transfer that to my cooling rack or counter. Once cookies are at room temperature, transfer to airtight containers, stacking as needed with parchment or wax paper in between. Refrigerate until completely chilled (30 minutes to 1 hour) or freeze for up to 3 months. When ready to serve, frost and enjoy!
To make the frosting, simply mix the butter, milk, vanilla and powdered sugar together until light and fluffy. Scrape the sides and mix again to ensure its smooth and the consistency you want. You want the frosting to be thick and able to hold its shape, while still soft enough to easily stir with a spoon or butter knife. Stir in the red food coloring.
If you're storing your cookies in the fridge, you can simply remove, frost and store in a single layer on parchment paper lined baking sheets until the frosting is mostly set. Then transfer them back into those airtight containers, layering with parchment or wax paper. Store in the fridge for up to three days.
If you're storing your cookies in the freezer, you can easily frost the frozen cookies right from the freezer and then transfer them to the fridge to completely defrost in a single layer on the baking sheets, gently covered with plastic wrap as described above.
Flour is arguably the most important ingredient in this recipe. Adding too much or not enough flour will make or break these cookies. That is why I was so specific in weighing my flour. If you do not have a kitchen scale, you will want to whisk your flour well to aerate it before measuring. After you aerate your flour, you will want to spoon your flour into the measuring cups, level the top and pour into your mixer. 630 grams is equal to 5 1/4 cups. Most people will end up with too much flour in their cookies if they aren't using a scale. Measure 5 cups first before adding the last 1/4 cup. A Note about Almond Extract-back in my good ol' college days, the original Swig Cookies were never made with almond extract. Today, the cookies don't have almond extract but the frosting does! If you like the flavor of almond extract, add 1/2 teaspoon to the frosting with the vanilla.