Line two baking sheets with parchment paper. Place 1.5 cups of Cinnamon Toast Crunch in a zip-top bag and crush with a rolling pin until you have coarse crumbs with some larger pieces remaining. Set aside 0.5 cup of whole cereal pieces for pressing on top later.

In a small bowl, stir together 1/4 cup granulated sugar and 2 teaspoons cinnamon until well combined. Set aside.

In a large bowl using an electric mixer, beat softened butter, brown sugar, and 1/2 cup granulated sugar on medium-high speed until light and fluffy, about 3 minutes. Scrape down the bowl as needed. The mixture should look pale and creamy.

Beat in eggs one at a time, mixing well after each addition, then add vanilla extract and beat until combined.

In a separate bowl, whisk together flour, 1 teaspoon cinnamon, baking soda, and salt. With mixer on low, gradually add flour mixture to butter mixture until just combined. Fold in the 1.5 cups crushed cereal with a rubber spatula. The dough will be thick and slightly sticky.

Cover dough and refrigerate for 15 minutes while you preheat the oven to 350 degrees F. This firms up the butter so the cookies hold their shape.

Using a 1.5-tablespoon cookie scoop, portion dough and roll into balls. Roll each ball generously in the cinnamon-sugar coating, then place 2 inches apart on prepared baking sheets. Press 2-3 whole cereal pieces into the top of each cookie.

Bake for 10-12 minutes, rotating pans halfway through, until edges are set and centers look slightly underdone. The cookies will look puffy and pale in the centers - this is correct. They will settle as they cool.

Let cookies cool on baking sheets for 5 minutes, then transfer to a wire rack to cool completely. The centers will finish setting as they cool, leaving you with chewy middles and crisp edges.