In a heavy-bottomed shallow pot over medium heat, warm 2 tablespoons of the olive oil. Add the onion and garlic and cook, stirring occasionally, until translucent, about 2 minutes. 

Add the farro and cook, stirring, until it smells toasty. Add the squash, thyme, bay leaf and sage, and season with salt and pepper. Add the sherry and cook until the wine has reduced by half, about 30 seconds. 

Add the stock and continue to simmer until the farro has puffed and is tender and the acorn squash is soft, 15 to 20 minutes. Adjust the seasoning with salt and pepper. If the ragout is too thick, thin it with more stock. The end result should be a loose farro with just enough reduced liquid to add a silky creaminess to the dish. 

The farro can be finished with butter and/or Parmesan. 

Preheat the oven to 350°F.

Season the pork with salt and pepper. In a large Dutch oven or other heavy ovenproof pot over high heat, warm 2 tablespoons of the olive oil. Being careful not to drop the meat and splatter the oil, add the pork in a single layer and cook, turning as needed, until browned on all sides. Transfer to a plate. 

Add the onion and garlic to the pot and cook, stirring occasionally, until starting to soften. Return the pork to the pot and add the thyme, sage, juniper berries, brown sugar and wine. Simmer until the liquid is reduced by half, then add the stock. 

Transfer the pot to the oven and cook for 3 hours, stirring every 30 minutes and checking to see if more liquid is needed. At this point, the meat should be fork-tender and falling apart, with the liquid reduced to about 1 1/2 cups. Transfer the pork to a cutting board and using 2 forks, pull the meat apart.  

Serve the pork and its juices over the farro ragout.