Winning / losing endgame practical vs theoretical when playing to improve

This isn't a game analysis question but more of a high level question.

Sometimes, stockfish tells me I blunder (and go from winning to losing) when I try to force the position into an endgame that I (erroneously) thought was winning. However, I end up converting the (theoretically lost) position. When I analyze further with stockfish, stockfish is always right but its moves are hard to find. However, my opponents are rarely playing as well as stockfish, so should I try to play for moves (that stockfish says are bad) that seem to be winning at my current level but objectively bad, or should I try to avoid them. And on the topic of stockfish, how can I develop a better sense as to who is for choice in those 0.0% positions? I'm playing to improve at chess, not to win as many games as I can.

You wont have stockfish in a real game, if you think a position is winning then go for it.

You should always try to play the strongest move and not just that convert into a theoretical endgame that you know is winning and correct the reasons if the position isn't.......

The question is largely irrelevant, because during the game you will not know what the engine says.

But generally, you should avoid playing moves that objectively change the result. Don't play a move after which your opponent has the chance to draw or even win if he finds the correct response.

That being said, you should not aim to play the top engine recommendation all the time. You rather want to play the move that makes the win most easy for you, and leaves your opponent with no hope. That could mean simplifying into a much easier ending, even if this means giving back some of your material advantage.

Of course, there may be rare occasions where you might want to try "for a cheapo" even if it means you might draw or lose. For example, you only have seconds left on the clock and any win by normal means would take many more moves. Or you have a safe draw, but tournament situation dictates you must play for a win.

But again, those are rare exceptions. Don't give your opponents chances. They will take them rather sooner than later, and at that stage of the game, they are very motivated to find them.

As to who is better in those drawish 0.00 positions... this is a matter of experience. Sometimes it is easy to see that one side is defending, while the other is attacking. Or one side has much easier play (easy to find a plan and good moves). Which side would you rather like to play? It is ok to have preferences. One useful indication is "Can you still improve the position?"

Yes I'm aware that I don't have access to stockfish during games, but I often analyze games where I have something as low as 75% accuracy, and in analysis I can try to play more like stockfish or try to play more like the games I won. Your advise that I shouldn't play moves that change the outcome, but I can generally play non-top moves if they stay in the same range (winning/drawing), is a very useful one.

On the useful indication of "can you still improve": is that a good thing or is it a sign of a bad position since it can be improved? I'm guessing you meant it as a good thing because it means there's a plan?

@sjcjoosten said in #5:
> and in analysis I can try to play more like stockfish or try to play more like the games I won.

If you could simply decide to play like Stockfish, this would make things so much easier. I mean it's not like you sit there and think "This move is the best, but Stockfish would play the other one and win".

Sometimes we have the feeling that objectively some other move might be better than our choice, but what we play gives us reasonably good chances. I think that is ok, as chess is a practical game between humans, but those decisions should not be taken lightly if they come with a potential downside.

For example, if you have a forced way to go to a Bishop+Knight ending, a theoretical win, but you never practiced it, it may be a good choice to keep material on the board instead, even if it might be objectively drawn at that point.

The better you get, the more moves will be approved by stockfish. Playing good moves is the best we can aim for. Learning which moves (or positions) are good is a life long task.

There is one more thing... if you are lost anyway, just following the best engine line is often simply the longest way to sure death. Playing suboptimal moves which create problems and tricks is most likely what you are looking for.

Sometimes you have the option to give your opponent the difficult choice between moves. If this comes at no or little cost, this is what you're looking for. You don't want to degrade your position on every move, but little differences in evaluation like 1.1 vs 1.3... those values usually mean very little.

> On the useful indication of "can you still improve": is that a good thing or is it a sign of a bad position since it can be improved? I'm guessing you meant it as a good thing because it means there's a plan?

It is usually a good thing. If you cannot improve your position any longer, you obviously cannot win. If neither side cannot improve, it's a draw.

As a side note, I recently played in an OTB tournament a move that I thought would not be best, but is very reasonable, and comes with a little threat. It worked and won the game on the spot on move ten basically. But it wasn't a cheapo that ruined my position otherwise. Those are the moves I like. :-) SF later said the move was ok and within the top three choices anyway; order depends on the search depth.

One more thing to consider: finding "only moves" is not synonymous with hard to play. Frequently it is much harder for the winning side to find their only winning moves, than to find the (forced) only moves for the defending side.

Man, chess is hard. ;-)

Just to add one more thing to some very good points made so far. (EDIT: nadjarostowa actually said it in a slightly different way at one point in #6 but I'll emphasize it anyway)

You should indeed not be making moves that change the objective outcome, but if you already have a significantly worse or lost position, play actively, not passively. For example, an endgame three pawns down where you have active pieces and you're giving your opponent something to worry about, offers more practical chances than an endgame only two pawns down in which you are just defending your remaining pawns and your opponent can win at leisure. If the position is lost, don't be afraid of sacrificing incorrectly in order to mix things up.

very Good Question. The thing is in such Questions is to Sense a Position, not logicly calculate, because of just to calculate without sense of Understanding that is convinient for You, the Idea won't be catched, and only remains the fact that SF did it well. Need a Selfishness in such dissasable, You may try to go your way, and see SF Branches, if something seems unclear, or You want to check something according to You Board View and Sense

@nadjarostowa said in #6:
> Sometimes you have the option to give your opponent the difficult choice between moves. If this comes at no or little cost, this is what you're looking for. You don't want to degrade your position on every move, but little differences in evaluation like 1.1 vs 1.3... those values usually mean very little.

Add to that if you have a winning position you can (should?) make the safer choice, that sometimes means a suboptimal move. For instance, when both players have several pieces so you simplify to get a winning pawn endgame (make sure it is so!) instead of a hard to find mate in 9 (this is the same @Brian-E said, but from the winning point of view).

@sjcjoosten said in #1:
> stockfish is always right but its moves are hard to find.

....yeah, thats the challenge