To Make the Dulce de Leche:

1. Remove labels from each can and place them in the bottom of the pot on their sides.
2. Fill the pot with enough water to cover the cans. There should be at least 3” of water over the cans to start.
3. Bring the water to a boil, then quickly reduce to low heat. Cover the pot with a lid and continue cooking on low heat for 2-3 hours, checking every 30 minutes to ensure that there is at least 2” of water over the top of the cans. 
4. After 2-3 hours, carefully remove the cans from the water. They will be hot! Allow them to come to room temperature on the countertop, then place in the refrigerator to cool completely. Do not open until after refrigeration.

To Make the Cake:

1. Turn on your oven to a true 325°F. A true 325°F is necessary in order to get a great bake on this cake. You can check your oven with an oven thermometer.
2. Place butter and dulce de leche into a large mixing bowl or the bowl of a stand mixer. Set aside.
3. Place the granulated sugar and vanilla beans in a medium bowl or deli cup. Either massage the vanilla beans into the granulated sugar with your fingers, or close the deli cup with a lid and shake to your heart’s content. This releases the vanilla essence into the granulated sugar. Set aside.
4. Sift together the all-purpose flour, baking soda, and kosher salt. Set aside.
5. Mix the butter and dulce de leche together on medium speed until they combined and smooth. Scrape the bowl as needed to ensure even mixing; this is very important for this recipe because the dulce de leche will tend to stick to the bowl. 
6. Add the vanilla-infused sugar and cream together until light and fluffy.
7. Add eggs, one at a time, mixing each one until it is fully incorporated before you add another egg. Scrape the bowl as needed to ensure even mixing.
8. If using vanilla extract, add it after the eggs are fully incorporated. Scrape the bowl and then mix until the vanilla extract is fully incorporated. If you are using vanilla bean, you can skip this step.
9. Add half of the sifted flour mixture and mix until nearly incorporated.
10. Add all of the pineapple and mix until nearly incorporated.
11. Add the other half of the sifted flour mixture and mix until nearly incorporated. Use a stiff spatula to scrape the bottom and sides of the bowl, and  gently fold together the batter until it is fully mixed and smooth-ish (the pineapple will prevent the batter from being completely smooth).
12. Prepare a 10- or 12-cup bundt pan as you normally would. I prefer butter and flour, but if you’re using a baking spray, use a pastry brush to spread an even, thin layer over the inside of the bundt pan.
13. Place the prepared batter into the bundt pan and gently tap the pan on the countertop several times to get rid of any air bubbles and to help the batter find its way into the intricate details of the bundt pan.
14. Place the bundt pan on a rimmed baking sheet and bake at 325°F for 65-75 minutes. The cake is done when it reaches an internal temperature of 212°F.
15. Remove the cake from the oven to a cooling rack. Wait ten minutes, then invert the cake onto the cooling rack to cool completely.

To Make the Simple Syrup:

1. Place the granulated sugar, water, pineapple juice, and fine sea salt in a small saucepan.  Bring to a simmer over medium-high heat. Turn off the heat once all of the solids have dissolved. The simple syrup will be watery.
2. Remove from the heat and stir in the pure vanilla extract. Place in a heat-resistant container and set aside to cool completely.

To Make the Dulce de Leche Glaze:

1. Place the room-temperature dulce de leche in a medium bowl. Whisk with a small whisk until it is smooth.
2. Add the confectioner’s sugar, fine sea salt,  and 1 tablespoon of whole milk. Stir until the mixture is fully incorporated. If necessary, add up to one more tablespoon of milk, 1 teaspoon at a time. The final glaze should have the consistency of thick honey.
3. Once the cake and simple syrup are completely cooled, use a pastry brush to brush the simple syrup over the entire cake. Then, pour the glaze over the cake and enjoy!