For the cream diplomat:

1. Heat the milk, vanilla, orange zest, cherry syrup, and salt in a heavy bottom saucepan on medium-low heat until it starts to simmer. 
2. While the milk is cooking, whisk the sugar and cornstarch together in a medium bowl. Quickly whisk in the egg yokes and keep whisking until the mixture is light and a little foamy. 
3. Slowly add 1/3 of the milk mixture a little bit at a time into the whisked egg yolks. Keep whisking until it's all well mixed. This tempers the eggs so that they don't curdle)  
4. Pour the egg mixture back into the pot with the remaining milk. Turn the heat up to medium and cook while whisking until it reaches a pudding-like consistency and is lightly boiling.   
5. Transfer the mixture to a bowl and add in the butter one tablespoon at a time. Whisking until each tablespoon is fully incorporated before adding the next. 
6. Cover the mixture with plastic wrap and press it directly into the top of the pastry cream. This prevents a film from forming on top. Place in the fridge to set for four hours. 
7. Once the pastry cream is set, make the bourbon whipped cream by beating the heavy whipping cream and bourbon until it reaches the soft peak stage. 
8. Fold the whipped cream into the pastry cream until it's been fully incorporated. Set in the fridge until you are ready to pipe it. 

For craquelin 

1. In a small bowl, combine the brown sugar and softened butter with a spatula until it reaches a paste. Add in the flour and mix until the flour is fully incorporated. 
2. Roll out the craquelin dough between two sheets of parchment paper until it reaches 1/8 inch thickness. Chill for 15 minutes. Once chilled, use a 1 inch round cutter and cut out 20-30 rounds. Transfer the rounds to plate and chill until you are ready to use.

For the choux pastry 

1. In a medium saucepan, heat the milk, water, bourbon, sugar, and butter and bring to a boil. Stir until all the butter has melted. 
2. Add in the flour and stir with a wooden spoon until a soft dough ball forms. Keep mixing the dough around the pan for 2-3 minutes to cook the flour fully. 
3. Move the dough to the bowl of a stand mixer fitted with the paddle attachment. Turn the mixer on top medium and add the eggs in one at a time. Allow each egg to be fully mixed before adding the next one. After you add the first two eggs, lightly beat the remaining one and it in 1/4 at a time. Keep mixing until your dough is glossy but thick enough to hold a V shape at the end of the paddle (see photo). I used 2 1/2 eggs in total. 
4. Preheat your oven 425 and line two baking sheets with parchment paper. 
5. Transfer your choux pastry to a pastry bag and cut off the end. Pipe the dough into 1 inch mounds about 1 1/2 inches apart. You should be able to pipe 20-30 mounds. After your dough is piped, add your cut craquelin rounds to the top of each mound. 
6. Place your baking trays in the oven and turn the temp down to 375. Bake for 30- 35 minutes or until the puffs are risen and are golden brown. 
7. Turn off the oven and let the puffs cool for 15 minutes with the door open. Remove the trays from the oven and let the puffs finish cooling.

Assembly 

1. Once the puffs have cooled, cut the tops off with a knife. 
2. Fill another pastry bag with the diplomat cream and pipe the cream into the puffs. Add the tops back on and garnish with orange slices and cherries.