For the Cupcakes: 

Adjust the oven rack to middle position and heat oven to 350°. Spray muffin tin with cooking spray, flour generously and tap the pan to remove excess flour.

Using an electric mixer on low speed, combine the flour, sugar, baking powder and salt, in a large bowl. Add the butter, one piece at a time, and combine until the mixture resembles coarse sand. Add the eggs, one at a time, and mix until combined. Add the milk and vanilla, increase the mixer speed to medium, and mix until the batter is light and fluffy and no lumps remain, about 3 minutes.

Pour the batter into a muffin tin lined with cupcake liners, filling each 2/3 of the way up. Bake until the cupcakes are golden and a toothpick inserted into the middle comes out clean, 18 to 22 minutes. Remove from oven and let cool.

For the Frosting: 

Using a stand mixer fitted with a whisk attachment, whip the butter on medium-high speed until smooth, about 20 seconds. Add the confectioners’ sugar and salt and mix on medium-low speed until most of the sugar is moistened, about 45 seconds. Scrape down the bowl; add the heavy cream, vanilla, the finely diced tart cherries, filling from the canned tart cherry pie filling, and orange zest. Whip on medium-high speed until light and fluffy, about 4 minutes, scraping down the bowl as needed.