Slow-Simmered Beef Stifado with Red Wine and Cinnamon

By AislePrompt Test Kitchen · Reviewed by AislePrompt Editorial · ·

A hearty Greek beef stew slowly simmered with aromatic cinnamon, tomatoes, and red wine, perfect for cozy dinners. This greek-inspired beef ready in about 170 minutes pairs beef chuck, cut into 1-inch cubes, olive oil, onions small pearl onions, peeled for a weeknight-friendly dinner that comes together with one pan and minimal cleanup. Each serving lands at about 450 calories and feeds 6, so it slots cleanly into a weekly meal plan and pairs well with a quick salad or grain on the side. Tap "Plan a meal with the AI" below to drop this recipe into your week and send the ingredients straight to Instacart. Nutrition values are approximate, calculated from USDA FoodData Central (fdc.nal.usda.gov) — verify against ingredient labels for any health-driven dietary plan.

Prep: 20 min Cook: 150 min Serves 6 Greek cuisine 450 cal/serving
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Ingredients

Instructions

  1. Step 1: Heat 3 tbsp olive oil in a large heavy pot over medium-high heat. Add 2 lbs beef chuck cubes and brown on all sides for 8-10 minutes.
  2. Step 2: Add 20 peeled small pearl onions and sauté with the beef for 5 minutes until onions begin to soften.
  3. Step 3: Stir in 3 minced garlic cloves and 2 tbsp tomato paste; cook for 2 minutes until fragrant and tomato paste darkens slightly.
  4. Step 4: Pour in 1 cup dry red wine and 1 cup beef broth, scraping the bottom of the pot to deglaze.
  5. Step 5: Add 1 1/2 cups crushed canned tomatoes, 1 tsp ground cinnamon, 2 bay leaves, 1 1/2 tsp salt, 1 tsp black pepper, and 1 tsp sugar. Stir well.
  6. Step 6: Reduce heat to low, cover, and simmer gently for 2 to 2 1/2 hours until beef is tender and sauce thickens, stirring occasionally.
  7. Step 7: Remove bay leaves before serving with crusty bread or over creamy mashed potatoes.

Equipment for this recipe

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Frequently asked questions

How long does Slow-Simmered Beef Stifado with Red Wine and Cinnamon take to make?

Total time is about 170 minutes (20 min prep + 150 min cook). Most home cooks find this fits comfortably into a weeknight; double the batch on Sunday for two dinners.

How do I store leftover Slow-Simmered Beef Stifado with Red Wine and Cinnamon?

Cool to room temperature within 2 hours, then store in an airtight container in the fridge for up to 4 days. Reheat covered in a 350°F oven for 10-12 minutes, or microwave at 70% power in 60-second bursts to keep olive oil from drying out.

Can I substitute ingredients in Slow-Simmered Beef Stifado with Red Wine and Cinnamon?

Yes — most ingredients in this recipe have flexible swaps. For oil, use any neutral high-smoke-point oil (avocado, grapeseed, refined coconut). For aromatics, dried herbs at ⅓ the volume of fresh work in a pinch. The full ingredient list is shoppable on Instacart so you can see substitutes in real time.

How do I scale Slow-Simmered Beef Stifado with Red Wine and Cinnamon for a different number of people?

The recipe is written for 6 servings. Multiply each ingredient by (your serving target / 6). Cook time stays roughly the same up to 2x; for 3-4x batches, switch from a skillet to a sheet pan or stockpot so the food isn't crowded — overcrowding steams instead of browns.

What goes well with Slow-Simmered Beef Stifado with Red Wine and Cinnamon?

Greek beef like this pair well with a simple grain (rice, couscous, or crusty bread), a quick salad with acid (lemon vinaigrette, pickled onions), and a pan sauce or yogurt-based dip. Tap "Plan a meal with the AI" to get specific side suggestions.