Brad's Marinated Flank Steak & Ravioli Marinara.

You can cook Brad's Marinated Flank Steak & Ravioli Marinara using 32 ingredients and 8 steps. Here is how you cook it.

Ingredients of Brad's Marinated Flank Steak & Ravioli Marinara

1. It's of For the steak.
2. You need 3-4 lb of flank steak.
3. Prepare 3 cloves of minced garlic, divided.
4. Prepare 2 tbs of olive oil.
5. It's 1/4 cup of red wine, I used cabernet.
6. It's of Sea salt and white pepper.
7. Prepare 1/2 tsp of rubbed sage.
8. It's 1 tsp of red chili flakes.
9. You need 2 tbsp of balsamic vinegar.
10. Prepare 1 tsp of each, dry thyme, oregano, and parsley.
11. Prepare 3 of basil leaves, bruised.
12. You need 8 of lg crimini mushrooms, sliced thin.
13. It's 1 of medium sweet onion, sliced thin.
14. It's 1 tsp of brown sugar.
15. It's of For the ravioli.
16. Prepare of Proper servings of desired ravioli.
17. Prepare 2 of lg can crushed tomatoes.
18. You need 1 of medium can of fire roasted diced tomatoes.
19. Prepare 2 of small shallots, minced.
20. You need 3 cloves of minced garlic.
21. It's 1 tbsp of butter.
22. It's 4 of Roma tomatoes, cut into 1 " squares.
23. It's 2 of beef bouillon cubes.
24. It's 2 of chicken bouillon cubes.
25. It's 1 tbsp of olive oil.
26. Prepare 1 tbsp of balsamic vinegar.
27. Prepare 2 tbsp of sugar.
28. It's 1 tsp of each, dried mustard, salt, pepper.
29. You need 1 1/2 tsp of each, dried oregano, dried thyme, chili powder.
30. You need 6 of lg fresh basil leaves, chopped.
31. It's 1 1/2 cup of red wine.
32. Prepare 1/2 cup of quality parmesan cheese, grated.

Brad's Marinated Flank Steak & Ravioli Marinara step by step

1. Marinate the steak. Add all ingredients for steak except mushrooms, 2 cloves garlic, onions, and brown sugar in a large ziploc bag. Mix well and add steak. Remove as much air from bag as possible. Place in fridge overnight..
2. When ready to cook, start with the marinara sauce. Heat a lg Dutch oven over medium heat. Add olive oil and shallots. Saute until shallots sweat off but do not brown. Add garlic and saute a couple more minutes. Add rest of ingredients except ravioli and parmesan cheese. Bring to a simmer and adjust seasoning to taste. Simmer at least an hour, covered..
3. Heat 2 lg frying pans over medium heat and get 4 qts salted water on to boil..
4. Add 1 tbs oil to each pan. Be careful when you add the steak to the pan. The oil may pop a bit. Add the mushrooms and onions to the other pan. Cook steak until it browned well on all sides. If pan is oven safe. Put into a 375 degree oven on the middle rack for 8-10 minutes. Saute mushrooms and onions until the water has sweated off..
5. Turn heat to medium low. Continue to saute until you start to see caramelization. Add remaining garlic and brown sugar. Saute until well caramelized..
6. Meanwhile cook ravioli per instruction. Drain and rinse in hot water..
7. Remove steak from oven and let rest for 5-7 minutes covered with foil. Slice..
8. Plate ravioli, top with sauce. Garnish with parmesan fresh basil and olives (optional). Plate sliced steak. Top with onions and mushrooms. Serve immediately. Enjoy..