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The late middlegame/early endgame is by far my weakest point.

I often get some kind of advantage in the opening, but then struggle to convert. I do study endgames, for example I am currently reading Silmans Endgame Course. But the point is that these kind of endgames that you can learn by rote memorization/technique (e.g. say Lucena Position, or K+P vs K etc.) is not what I struggle with. It's rather to find the right plan in positions, where there are many more pieces on the board.

I try to give an example by some positions that I encountered in tournament games, e.g. longer time controls. I hope this explains better in what kind of positions I struggle.

r1r3k1/ppp2pp1/2q2n1p/4B3/8/2Q4P/PPP2PP1/3RR1K1 w - - 0 19



1. Qxc6 bxc6 Bxf6 gxf6

I noticed by exchanging pieces, that black will end up with several pawn islands and double pawns. But I failed to convert. Later

8/p1p2p2/1rp2k1p/4Rp2/1PP2P2/P6P/6P1/6K1 w - - 0 29



1. Kf2

instead of Ra5, forcing on exchanging rooks, or attacking both the a and c pawns. I simply didn't have a proper plan here and what to do - so even though I can calculate, I did not know what to calculate. In this game black managed to ourmaneuvre me and I could barely hold a draw.

8/1p1k1p1p/2n1p1p1/p1P5/1pK1PP2/1P6/1B4PP/8 w - - 0 36



1. g4? 

here I played g4? instead of seeing that I can invade with Kb5, and then Black is stuck with defending his a-pawn so that his Knight is almost not moveable. After Na7 I lost instead of securing a draw.

3r4/8/2Rnk1p1/7p/1P1p1B1P/2p2P2/5P2/6K1 w - - 0 40



1. b5?? 

which Black can answer with Kd5 and wins. I played b5?? instead of getting my King in the game with Kf1, which would have rescued the game.

In these positions it seems crucial to find the right plan before calculating anything. Typical endgame books kind of don't bring me forward I feel.

What kind of learning ressources and or methods can you suggest to improve in such kind of positions?

Knowing when/how to transition to an ending is one of the difficult choices. Ideally you will be able to correctly evaluate the resulting complex ending when making that choice. I find the most helpful thing in evaluating complex ending is knowing the simple endings. There are few resources I have found on this interesting topic.

There is a bit at the end of Silman's Complete Endgame Course on this.

Joel Benjamin's Liquidation on the Chess Board covers the transition to a pawn ending. Though that is from a piece ending to a pawn ending some of the ways of thinking are the same.

Your examples call for "technique" as in "and the win is now a matter of technique" Sadly these commentators rarely explain what the technique is.

Take your example of pawn islands / isolated pawns. Standard technique is to attack the pawns activating your pieces and tying your opponent's pieces to the defense of the pawns. But what to you do after he defends his pawns? Then another principle may come into play, 'alteration' or multiple weaknesses. Now you can switch you attack between weaknesses and make your opponent respond. Even if the position is drawn you can present your opponent problems and try to provoke an error. Sometime if you alternate your attack in just the right move order your opponent has no good response. This is often true when you have a space advantage. Sometimes a better position is just a draw. There are no simple rules to follow, only judgement and experience.

I agree with Ywapom that going over great endgames is a wonderful way to see the patterns and get an idea of what to try. I also agree that Karpov and Capablanca are good choices, they play very clear, the moves often look so simple. Have fun with the masters.

The English GM Glenn Flear has coined the phrase "not quite an endgame" or NQE to describe exactly the kind of positions you talk about. He has written a book, "Practical Endgame Play - Beyond the Basics: The Definitive Guide to the Endgames That Really Matter" about these. It covers NQEs where each player has pawns and only two pieces.

Unfortunately it is out of print but you may be able to find it for sale second hand.

There is a book: Endgame Strategy (Cadogan Chess Books)Apr 1, 1994
by Mikhail Shereshevsky which includes early endgame/late middlegame positions.

and: Capablanca's Best Chess Endings: 60 Complete GamesFeb 1, 1982
by Irving Chernev
is good.

Going over complete games of Karpov is beneficial for technique as well.