To Make the Cake:

1. Preheat oven to 325°F.  An oven thermometer will help you reach the right oven temperature; our ovens are often off, and that makes a huge difference!
2. Sift all-purpose flour, vanilla pudding, baking soda, and kosher salt into a medium bowl.  Set aside.
3. Add butter to the bowl of a stand mixer or a large mixing bowl.  Mix the butter until it is completely smooth.
4. Add dark brown sugar and cream butter and sugar until light and fluffy.  Take your time with this step!  (Not sure what properly creamed butter and sugar should look like?  Take a look here!)
5. Add eggs, one at a time, mixing until each egg is completely incorporated.  Scrape the sides and bottom of the bowl as needed.
6. Add the vanilla extract and maraschino cherry juice and mix until completely incorporated.
7. Add half of the flour mixture and mix until just incorporated.
8. Add all of the pineapple juice and mix until just incorporated.  The mixture might look a bit curdled at this point and that is okay!
9. Add the other half of the flour mixture and mix until just incorporated.  Finish with a few turns with a stiff spatula to ensure that everything is evenly mixed.

To Prepare the Pan:

1. Prepare the entire bundt pan as your normally would (I use the butter/flour method, and you can see how to do that right here!).  
2. Gently pour the melted butter over the bottom of the pan, making sure not to splash the sides.
3. Sprinkle the brown sugar into the bottom of the pan, making sure to cover all of the butter.
4. Place pineapple rings into the bottom of the pan.  Add cherries to the center of the pineapple rings.
5. Gently add the batter to the pan.
6. Bake for 60-75 minutes, or until an instant-read thermometer reads 210°F-215°F.  My Goldilocks temp is 212°F. 
7. Remove from the oven and allow to place on a cooling rack, in its pan, for ten minutes.  Place a piece of parchment paper under the cooling rack!
8. After ten minutes, invert the cake onto the cooling rack and watch the goodness happen!

To Make the Simple Syrup:

1. Add the water, granulated sugar, and salt to a small saucepan.  Bring to a boil and boil just until all of the solids are dissolved.  Remove from the heat.
2. Add the pineapple juice and stir to combine.
3. Gently brush on the parts of the cake that are not covered by the brown sugar “caramel” from baking (just the bottom parts of the cake).  
4. Allow the cake to cool completely before cutting and 
5. eating! (3-5 hours)