Preheat the oven to 400F.
Slice the squash, longways across.
Place cut side down on a 15x10 rimmed baking sheet and bake for 1 hour.
Add the ground beef to a 5 quart pot over medium heat and brown the meat. Be sure to stir to break up the meat while browning.
Add all remaining ingredients and stir to combine.
Cover and cook for 10-15 minutes to heat throughout and let the flavors combine.
Turn heat to low and leave cover on until squash is finished cooking.
Remove squash from oven, flip over and using a fork, scrape the insides away from the outer edges.
Pour Sloppy Joe mixture into the squash and serve. If serving as a sandwich, serve a heaping scoop of Sloppy Joe on Paleo Bread with a garnish of squash and even more squash on the side.
Enjoy!