Preheat the oven to 375°F and grease a small pan with olive oil. The pan should fit two halves of squash placed side by side.
Break 2 slices of bread into pieces and soak them in ½ cup milk for 5 minutes.
Remove the crust of the bread and break it into crumbs with your hands or a food processor. Leave the crust crumbs aside for topping. Squeeze the bread slices to wring out most of the milk.
Mince 2 cloves garlic and ¼ cup parsley. Remove 4 links Italian sausage meat from the casing.
Meanwhile, cut 1-2 medium red Kuri squash in half and remove the fibers and seeds. You may only need 1 squash if your squash is larger (in which case, halve each half for a total of 4, if feeding 4).
Slice a sliver off of the bottom of each squash half so the halves sit flat, then place them in the oiled pan.
In a large mixing bowl, add the sausage, bread crumbs, garlic, parsley, and 2 tsp. crushed red pepper in with 1 egg, and mix well.
Add a little salt to the mixture, if necessary. Be careful not to oversalt, as your Italian sausage may already have a high salt content.
Stuff your squash halves with the Italian sausage mixture.
Top with the breadcrumbs and sprinkle with olive oil and ½ cup grated cheddar.
Roast in your preheated oven for about 30 minutes covered with aluminum foil, and then another 30 minutes uncovered, until the squash is tender when you poke it with a fork. The cheddar on top should be a nice golden brown.