Combine 1/4 cup wine with cherries; let stand 10 minutes. Meanwhile, cut steak into 4 serving-size pieces; pound with a meat mallet to 1/4-in. thickness. Using 1/2 teaspoon salt and 1/4 teaspoon pepper, season both sides.
Select saute setting on a 6-qt. electric pressure cooker and adjust for medium heat. Add 1 Tbsp. oil; cook onion until tender. Add garlic; cook 1 minute longer. Press cancel. Transfer to a large bowl; stir in bread crumbs, olives, cheese, basil, cherry mixture and remaining pepper. Crumble sausage over bread crumb mixture; mix well.
Divide the sausage mixture into 4 portions; spread evenly over each steak piece. Roll up steaks jelly-roll style, starting with a long side; tie with kitchen string.
Select saute setting and adjust for medium heat. Add remaining oil; brown meat on all sides. Top with marinara sauce and remaining wine. Press cancel. Lock lid; close pressure-release valve. Adjust to pressure-cook on high for 15 minutes. Allow pressure to naturally release for 10 minutes, then quick-release any remaining pressure. Serve with pasta.
Test Kitchen tips
Mild Italian or turkey Italian sausage can be used in place of hot Italian sausage.