Pinapple Squash

Acorn squash halves make natural little bowls, and filling them with crushed pineapple and a dusting of cinnamon turns a humble vegetable into something that tastes almost like dessert.

The water bath is what makes this work. That half inch of hot water in the baking dish creates steam under the foil cover, cooking the squash evenly from the outside in. Without it, the bottoms dry out and the tops stay tough. An hour in the oven and the flesh should be soft enough to scoop with a spoon.

Crushed pineapple with its juice keeps everything moist as it bakes, and the natural sugars in both the squash and pineapple caramelize slightly at the edges. No added sugar needed, which is why this works so well as a diabetic-friendly side.

Chef Tips

• Trim just enough off the bottom of each squash half so it sits flat. Cut too much and you’ll create a hole that leaks pineapple juice everywhere.
• Use unsweetened crushed pineapple with the juice included. That juice steams inside the squash cavity and keeps the flesh from drying out.
• Check for doneness by piercing the thickest part of the squash wall with a fork. If there’s any resistance, give it another 10 to 15 minutes.
• Cover the pan tightly with foil. Loose foil lets steam escape and you’ll need significantly longer cooking time.

Variations

• Swap pineapple for diced pears or apple chunks with a sprinkle of nutmeg for a fall-inspired version.
• Add a drizzle of maple syrup in the last 10 minutes for a glazed finish when you’re not watching sugar intake.
• Sprinkle toasted pecans over the top right after baking for a crunchy contrast to the soft squash.