In a medium pot over medium-high heat, bring the broth to a simmer.
In a large, heavy bottomed pot over medium heat, add the olive oil and butter. Once the butter has melted, add the onion, garlic, and minced rosemary, stirring occasionally. Cook until the onions are soft and translucent.
Add the rice, stirring to coat each grain with the butter and oil. Stirring fairly constantly, wait until the rice smells nutty. That lets you know that the rice has been toasted a bit. And this means flavor.
A couple of ladles at a time, add the warmed broth to the rice. Stir constantly. Once the liquid has been absorbed, add another couple of ladles. More stirring. Repeat this until most or all of the liquid had been incorporated and absorbed, and the rice has a nice tender bite to it. You may not use all of the broth.
Add the mashed squash, stirring to incorporate. Add the cheeses, stirring to combine. Add salt and pepper to taste, along with the cubed squash.
Garnish with fresh rosemary, if desired.