1. Preheat oven to 350°F (176°C) and prepare a 9×13 inch cake pan with non-stick baking spray.
2. Add the flour, sugar, cocoa, baking soda, baking powder and salt to a large mixer bowl and combine. Set aside.
3. Add the milk, vegetable oil, vanilla extract and eggs to a medium sized bowl and combine.
4. Add the wet ingredients to the dry ingredients and beat until well combined.
5. Slowly add one cup of red wine to the batter and mix on low speed until well combined. Scrape down the sides of the bowl as needed to make sure everything is well combined.
6. Pour the batter into the prepared cake pan and bake for 29-32 minutes, or until a toothpick comes out with a few moist crumbs.
7. Remove cake from oven and poke holes all over. I use a knife sharpening rod, but you could also use a straw.
8. While the cake is still warm, add the chocolate chips to a medium sized bowl. Set aside.
9. Add the sweetened condensed milk a microwave safe measuring cup. Heat heat the milk until it begins to boil, then add the remaining 1/2 cup of wine and stir to combine. Pour the hot mixture over the chocolate chips.
10. Whisk the chocolate until smooth, then immediately pour over the cake, spreading it into the holes. Don’t let the mixture sit before pouring it over the cake or it’ll start to thicken and not soak in the holes as well.
11. Set the cake in the fridge to cool and soak.
12. To make the whipped cream, add the strawberries and water to a food processor or blender and puree until smooth, then strain through a fine mesh sieve to discard the seeds.
13. Add the puree to a medium sized saucepan and cook over medium heat. Allow the mixture to come to a boil and continue to boil, stirring consistently to keep it from burning, until it has thickened and reduce to 1/4 cup, about 15 minutes. To measure, pour the puree into a measuring cup. If it’s more than 1/4 cup, add it back to the pan and continue to cook it.
14. When the puree has thickened and reduced, pour into a small bowl and refrigerate until completely cooled. This strawberry mixture can be made ahead, if you like.
15. When cooled, add the strawberry mixture, heavy whipping cream and powdered sugar to a large mixer bowl and whip on high speed until stiff peaks form. Be sure to use the full amount of powdered sugar, which helps stabilize the whipped cream.
16. Pipe the whipped cream onto the cake to create rosettes (I used Ateco tip 844), or just spread the whipped cream onto the cake.
17. Refrigerate the cake until ready to serve. This cake is great to make ahead and could be made 1-2 days ahead and then stored well covered in the fridge. Cake will be best for 3-4 days.