In a large nonstick pot, combine the milk, oil, and ¼ cup of sugar. Heat up to about 120F {warmer than body temperature but NOT burning hot} over medium heat, then remove from burner and sprinkle the yeast on top. Let the mixture sit for a few minutes to allow the yeast to activate.

Afterwards, mix in the 2 cups of flour, cover the pot with a clean tea towel, and let the dough rise for about 1 hour.

After the first rise, add in the salt, baking powder, baking soda, and additional flour. Knead until all the flour has been absorbed, and add more if needed. You want the dough to be soft and smooth but not too sticky! Using a sharp knife, cut an X on top of your dough {this helps it rise }, cover with a tea towel again, and let rise for an additional 3+ hours. You can let it rise overnight at this point, or you can also wait until the next step!

After the second rise, lightly flour a clean surface, and dump the dough on top. Knead it for 2-3 minutes, adding more flour as needed. The dough should be smooth and easy to work with, so add flour if it's too sticky!

Using a rolling pin, roll the dough out into a rough rectangle, making sure you don't roll it out too thin. Spread the softened butter all over the surface, then top with the brown sugar, cherry pieces, and chocolate chips.

Starting on the long side closest to you, roll up the dough, being careful that no filling falls out of the sides.

Using a large, smooth knife, cut 1½-2 inch slices of dough, and place them in a greased 9x13 pan {or you can use a giant muffin pan + 9x9 baking dish}. Make sure to leave some space between the rolls to allow them to rise more!

At this point, you can cover the pans with plastic wrap and either let them rise for 30 minutes in a warm place, or place them in the refrigerator overnight.

When ready to bake, preheat the oven to 375F. Bake the rolls 15-18 minutes, until the tops are golden brown and no longer doughy.

While the rolls cook, make the frosting. In a medium bowl, mix together the powdered sugar, vanilla extract, and salt, and add in the milk a little at a time until it reaches the desired consistency.

Let rolls cool, then drizzle with frosting. Enjoy!