Cut beef into two portions for individual servings. Set aside
Heat 1 TBS oil in pan. Saute onion and celery until onion is transparent.
Add in garlic and cherries. Cook for an addition few minutes. Transfer to crock pot.
Season beef with steak seasoning. Season the flour with salt and pepper. Dredge each piece of beef in flour.
Heat 1 TBS oil in pan and brown beef on all sides. Transfer to crock pot.
Add red wine to pan, reduce and deglaze.
Add brown sugar, balsamic vinegar, beef broth and Italian seasoning to the pan cook for a few minutes.
Pour over beef and cherry/veggie combo in the crock pot.
Cook on high for 5 hours or low for 8 hours.