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When I have this situation, I put the steak into the crockpot, surround it with the cooking liquid, and cook it all day if need be. I cook it on high for 1 or 2 hours in the crockpot (am just trying to make sure it is hot enough to begin with)and then switch to low.
For instance, if I take it out of the oven, it will certainly be hot if it goes directly into the crockpot. But if I've refrigerated it overnight, then it'll spend more time on 'high' in the crockpot.
Don't brown steak before cooking. Never had a problem, just put stewing steak in pyrex dish with a finely chopped onion, a little oil (rapeseed I use) and a couple of stock cubes. In oven about an hour or so at 200 deg, (depends on quantity - use common sense).
Juices make lovely gravy with gravy granules if desired. Always gets eaten. Served with mashed potatoes, 1 root and 1 green veg.
If it is cooked on a lower heat, very slowly for a few hours, it should not be tough at all. Usually, the slower meat is cooked, the more tender it is. So, it depends on your oven temperature.
I always dredge my stew meat in flour, first, then brown it,
in oil, bacon fat; then add water. wine, or broth/stock, cover and braise in oven or crockpot.
As long as it is cooked slow, it shouldn't be touch. The reason for browning is to give it a "crust" and the flour helps thicken the juice. It has nothing to do with flavor. I rarely brown my roasts and oven stakes before baking. As long as you add plenty of seasoning (I like to use onion soup mix), it should taste fine.
Ditto what 'perfumed fan' said below.
If it does come out too tough/dry...dont toss it:
Now that they have made pork chops so lean I can't cook a chop to save my life without being on the dry side. For some odd reason when I slice up the leftovers in small cubes and put it with the leftover stuffing bits and the gravy and microwave it the next day for lunch it is as moist as can be. You think the extra cooking the second time would make it even worse but it isn't. LOL.
It might be a little dry and lacking in flavor but it is edible. Make gravy to go with it.