Preheat your oven to 350°F (175°C). Line a 9x13-inch baking sheet with parchment paper, leaving overhang on two sides for easy removal.
In a large bowl, beat the softened butter, brown sugar, and granulated sugar together with an electric mixer on medium speed until light and fluffy, about 2-3 minutes.
Beat in the eggs one at a time, then add the vanilla extract, mixing until well combined.
In a separate medium bowl, whisk together the flour, baking soda, cinnamon, and salt. Gradually add the dry mixture to the wet mixture, mixing on low speed until just combined.
Using a spatula, fold in the rolled oats and raisins until evenly distributed throughout the dough.
Transfer the dough to the prepared baking sheet and press it evenly into a flat layer using your hands or a spatula. The dough should be about 1/2-inch thick.
Bake for 25-30 minutes, or until the edges are golden brown and the center is set. A toothpick inserted into the center should come out clean or with a few moist crumbs.
Allow the bars to cool completely in the pan on a wire rack, about 1 hour. This is essential for clean slicing.
In a small bowl, whisk together the sifted powdered sugar, milk, and vanilla extract until smooth. Adjust milk to reach a drizzling consistency.
Drizzle the icing over the cooled bars using a spoon or piping bag. Let the icing set for 10 minutes, then lift the bars out using the parchment overhang and cut into squares.