Preheat your oven to 350°F (175°C). Grease a 9x13-inch baking pan. For easiest serving, use a metal or glass pan with straight sides.
Prepare the cake: In a large bowl, combine the cake mix, eggs, oil, and milk (or water) per the box directions.
Add vanilla and cinnamon if using. Mix until smooth and no dry pockets remain.
Bake: Pour the batter into the prepared pan and bake 25–30 minutes, or until the top springs back and a toothpick comes out clean. Do not overbake.
Cool briefly: Let the cake rest 15–20 minutes.
It should still be warm, not hot.
Make the soak: In a bowl or measuring pitcher, whisk together sweetened condensed milk, evaporated milk, whole milk (or half-and-half), vanilla, and a pinch of salt until smooth.
Poke the cake: Using a fork or skewer, poke holes all over the surface, spacing about 1/2 inch apart. Go deep, but avoid tearing.
Soak: Slowly pour the milk mixture evenly over the cake, letting it absorb as you go. If it pools, pause for a minute, then continue until you’ve used it all.
Chill: Cover and refrigerate at least 4 hours, preferably overnight, to allow full absorption and flavor development.
Whip the topping: Beat heavy cream, powdered sugar, and vanilla on medium-high until medium-stiff peaks form.
Don’t overwhip.
Finish: Spread whipped cream over the chilled cake. Dust with cinnamon or add berries or coconut if you like.
Serve: Slice cold. The cake should be moist with a gentle, creamy soak in every bite.