Heat the oven to 350°F. Line baking sheets with parchment paper so the cakes release easily and keep their pretty shape.
In a large mixing bowl, add strawberry cake mix, eggs, neutral oil, flour and vanilla (if using). Stir until everything is combined and smooth. The batter should be thick and scoopable, more like cookie dough than runny cake batter.
Use a 1 1/2 tablespoon cookie scoop or a heaping tablespoon to scoop mounds of batter onto the prepared baking sheets.Space them about 2 inches apart, because they will spread into cute little cake rounds while they bake. Bake for 8 to 10 minutes, until the tops spring back when lightly touched and the edges look set. (Do not wait for browning, you want them soft and pale for that classic whoopie pie look. If they’re starting to brown, take them out of the oven immediately.)
Let the cakes cool on the baking sheet. When they’re completely cool and you’re ready to add the filling, carefully lift the whoopie pie rounds off the baking sheet. You may need a rubber spatula to gently pull them up.
In a medium bowl, beat the softened butter and cream cheese with a hand mixer or stand mixer for about 1 minute until creamy. Add your powdered sugar a cup at a time, plus vanilla extract. Beat until light and fluffy.
If the filling is too thick, add a splash of cream or milk. If it is too thin, beat in more powdered sugar a little at a time.
Pair up your cooled strawberry cake rounds by size so each sandwich looks neat and even.
Transfer the filling to a piping bag with a plain, round tip or just the tip snipped off. You can also just use a spoon or offset spatula.
Pipe or spread a generous layer of filling onto the flat side of one cake. Then, top with the flat side of a second cake and gently press to spread the filling to the edges. Repeat with the remaining cakes and filling.
Place the assembled whoopie pies in a single layer in an airtight container that’s lined with parchment paper. Refrigerate for 3 to 4 days; let them come to room temperature before serving so the cakes are soft and the filling is creamy.To freeze, layer whoopie pies between sheets of parchment in a freezer-safe container and freeze for up to 1 month. Thaw in the fridge overnight.