Steak & Sweet Dumpling Squash Chili

I really really love homemade chili, and starting paleo at first felt like a real bummer. What is chili without three different kinds of bean? Quite fabulous, as I discovered recently.

One of the best things about chili is that it’s such an all-encompassing term. I don’t think I’ve ever made a batch of chili that has come out exactly the same because I’m always changing it up based on what’s on sale, what I feel like, and what I remember to include. And, of course, if you are not a meat-eater or you HAVE to have beans in your chili, you can easily customize this recipe to fit your tastes.

The directions and cook time assume you’re using a crock pot, but you can easily make it on the stove top.


1 can stewed Italian-style tomatoes, chopped.

6 oz tomato paste

1 large carrot

1 sweet dumpling squash (or winter squash of your choice, about 2 cups worth), cooked

4-5 pearl onions, minced

2-3 cloves garlic, minced

1 large red bell pepper, chopped

1 lb sirloin steak, chopped and cooked (about medium-medium well)

1 Poblano pepper, chopped

1 Anaheim pepper, chopped

1 red Fresno chili pepper, chopped

1 Santa Fe pepper, chopped

1 tsp oregano

1 tsp cumin

1 tsp sea salt

1 tsp paprika

2 tsp cocoa powder

1 tsp parsley

1/2 tsp liquid smoke

 Paleo Cooking for the Modern Hungry Lady: Steak & Sweet Dumpling Squash Chili

The picture shows more peppers than the recipe calls for because I made a second batch chock-full of beans for my husband.


Working in batches if necessary, chop the peppers (including the bell pepper), onions, and garlic and saute them in a little coconut oil for a few minutes over medium-high heat, until they are a little soft and browning around the edges. Dump into the crock pot.

Cut the squash into quarters, remove guts and seeds, sprinkle with water, and microwave for 8-10 minutes or until fork-tender. Cut into about .5″ pieces and add to crock pot.

Chop the carrot as small as you prefer, add to crock pot.

Cook the steak in a little coconut oil over medium-high heat until the center is just a bit pink. Play around with seasonings here. I have used pre-seasoned steaks before because they were on sale, and the result is always great! Chop into 1/2 inch pieces and add to the crock pot.

Add tomato paste, chopped tomatoes (and all juice from can) and all seasonings to crock pot. Stir together well with other ingredients. Pop on the lid and let your concoction cook on HIGH for at least 4 hours. Putting it on low all day won’t hurt it.

Makes 3-4 Servings, depending on how hungry you are and how delicate you wish to appear in front of others.

 Paleo Cooking for the Modern Hungry Lady: Steak & Sweet Dumpling Squash Chili

Thank you Instagram, for making my poorly-taken photos look just a tiny bit better.


2 thoughts on “Steak & Sweet Dumpling Squash Chili

  1. Pingback: Cauliflower Hummus | Paleo Cooking for the Modern Hungry Lady

  2. Pingback: Salsa Verde + Cauli-rice Bake | Paleo Cooking for the Modern Hungry Lady

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