To Make Dough:
Using a stand mixer with a hook attachment, mix together milk, butter, egg, salt, and 3 cups of flour until well integrated, scraping down sides if needed. Slowly add in remaining 2 cups of flour, ¼ cup at a time, until dough comes together. Dough should be elastic but not stick to the sides of the bowl. Let dough rest for 30-60 minutes.
1. Divide dough into four even sections. Working with one section at a time, roll out dough on a lightly floured surface until it is about 1/16th of an inch thick. Use a 3 inch cookie cutter or glass to cut out circles of dough. Gently gather scraps and return to bowl with remaining dough.
2. Place two cherries in the center of each circle. Fold each circle in half and gently pinch the edges closed. Transfer finished dumpling to a lightly floured baking sheet and continue with remaining circles.
3. Repeat process with scrap dough and remaining sections until all cherries are used up. At this point, you can freeze the dumplings on the baking sheets. Once frozen, you can place them all in a ziplock bag and store for 3-6 months.
1. Bring a large pot of water to boil. Add dumplings (frozen or fresh) to water and stir, taking care not to overcrowd them (you may only be able to cook 20-25 at a time). Cook until the dumplings float to the top, about 5-7 minutes. Using a slotted spoon, transfer dumplings to a bowl.
2. Top dumplings with a little butter and sugar or sour cream to serve.