Heat your oven to 350 degrees.
Slice each squash in half, scoop out the seeds, and then slice the squash into half circles that are about an inch and half thick. Spread them out on a parchment lined baking sheet.
Whisk the melted butter, maple syrup, salt, and 2 tablespoon brown sugar together. Brush the mixture over the squash (there will be a little leftover - set aside for later). Roast the squash for 40 minutes.
Remove the squash from the oven, and flip it over. Brush the remaining butter mixture over (reheat it in the microwave to get the butter to melt again). Sprinkle the squash with the remaining brown sugar. Return to the oven for 20 minutes.
Spread the prosciutto out on another parchment lined baking sheet. Let cook for 12-15 minutes, until it has hardened. Then remove from the oven and let cool.
Once the squash is done roasting, place it in a serving dish and crumble the prosciutto over the top.