Heat 1 TBSP of the olive oil in a dutch oven or large pot over medium-high heat.
Add HALF the pork to the pot and cook, stirring occasionally, until pork is browned, about 5 minutes.
Transfer the browned pork to a plate then add another 1 TBSP of oil to the pot and cook the rest of the pork the same way.
Transfer all the browned pork to a plate and set aside.
Add the remaining 1 TBSP of oil to the pot then add the onion, bell pepper, and celery to the pot and cook, stirring occasionally, about 6 minutes.
Add the pork back into the pot then stir in the flour, paprika, garlic, thyme, oregano, cayenne, 1 tsp salt, and 1/2 tsp black pepper and cook while stirring for about 1 minute.
Stir in the milk and bring to a slight boil.
When the milk begins to boil stir in the macaroni then reduce heat to medium-low.
Place a lid on the pot and simmer over medium-low heat, stirring often, until pasta is tender, about 12 minutes.
Take the pot off the heat and stir in the shredded cheese until combined.
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