How should I have decided which side to attack on?

Question

I played black and was a pawn up. My plan was to castle on the opposite side from white's king, then use my majority on that side to pawn storm him. So on the turn shown below, I was about to castle long.

After we drew, I analysed the game with an engine, which preferred castling short and pushing the a-pawn, so it seems I should have done the exact opposite of my plan.

My question is, how should I have decided on which side to attack in this position? Why was my choice wrong?

Thanks in advance.

[FEN "r3k2r/1bp2ppp/pp2p3/8/8/2qPBP1P/P1P1Q1P1/R4RK1 b kq - 1 16"]

1. e4 e6
2. e5 d5
3. exd6 Bxd6
4. Nf3 Nf6
5. Bd3 b6
6. Bb5+ Nbd7
7. Nc3 Bb7
8. d3 a6
9. Bxd7+ Qxd7
10. O-O Ng4
11. h3 Ne5
12. Nxe5 Bxe5
13. Qe2 Qc6
14. f3 Bxc3
15. bxc3 Qxc3
16. Be3 O-O-O
17. Bd2 Qb4
18. Be3 Qc3
19. Qd2 Qxd2
20. Bxd2 Bc6
21. Bc3 f6
22. Rad1 Ba4
23. Rd2 e5
24. Rc1 g5
25. d4 exd4
26. Rxd4 Rxd4
27. Bxd4 Rf8
28. c3 c5
29. Bf2 Re8
30. Re1 Kc7
31. Bg3+ Kb7
32. Rxe8 Bxe8
33. Bd6 f5
34. g4 fxg4
35. hxg4 h5
36. Be7 hxg4
37. fxg4 Bd7
38. Bxg5 Bxg4
39. Kf2 Kc6
40. Ke1 Be6
41. a3 Kb5
42. Bd8 Ka5
43. Kd2 Ka4
44. Bxb6 c4
45. Bc5

Answer 1

You should castle "short" (on the king side). because you want to attack on the queen side without exposing your king.

1) White is short a pawn because of his missing b pawn. If you castle "long" and put your king on that side, White's open b file (and the black diagonal to b6) become compensation. If you don't, he's just a pawn down.

2) Your queen is powerfully placed on the queen side. You want to move up your pawns to support your queen, without exposing your king, or allowing your queen to be "pinned" by a rook. White has his queen on the king side and you don't, so it doesn't make sense to attack there.

3) Your best chances of getting an "outside" passed pawn are on the a and b files, so you want to advance those pawns, with your c pawn in support.

Answer 2

The question "on which side to attack?" is already flawed. In many positions, a direct attack isn't appropriate. For an attack to have good chances of success, you need some sort of advantage, such as a lead in development or extra space on one side of the board. You don't really have any advantages that would help you launch an attack on the kingside - arguably your bishop pointing that way, but it's not much. Your real advantage in this position is your extra pawn, which can eventually help you make a passed pawn in an endgame. Castling on opposite sides and going for a pawn storm is an extremely high risk strategy that doesn't have any positional factors supporting it, and doesn't exploit your advantage, the extra pawn. A good starting point in this position is getting your king to safety and getting the rooks in the game.

Answer 3

I look at this position and think:

1: you castle short because of the open b-file. 2: you play Rad8 and e5 to limit his bishop. 3: followed by things like f6 and Bd5 to reposition the black light-squared bishop.

Seems like a reasonable plan to me. I would not castle long in this position. Gives white to many attacking options. Not all positions call for direct attacks on the king position. this looks like one of them to me at first glance.

Answer 4

Bad question. You have no attack, especially on the king.

Castle 0-0 and get on with the game positionally. There is not enough material to do any attacking especially the king.

Castle long and White will have the attacking chances such as they are.

You are a pawn up but with bishops of opposite colors. This will be hard to win no matter what you do.

Answer 5

I had a similar (but not the same) question here.

Castling queenside would allow your four pawns and both rooks to push the opposing king, with support from the light square bishop. This would allow you to pose a big threat on the king, protected only by two pawns and a bishop facing four pawns, two rooks, and possibly a bishop. The white rooks and queen would be somewhat blocked from joining the action due to the white pawn structure, reducing white's chances of defending their king.

Castling kingside would allow you to push all of your pieces on the flank. Your queen is already there, and the three pawns, bishop, and rook could quickly launch an attack from the B and C files. The isolated pawn on A2 can possibly be taken, leaving white with 2 pawns against 3 on the queenside. Support from your major pieces and the bishop would create a solid attack, and trading would be an even greater disadvantage for white after A2 is taken.

Either way, it is technically possible to overcome white. It is unlikely that a human would be able to forsee the outcomes which the computer sees, and I cannot give an exact reason for why it would prefer short castling.

My suggestion is that perhaps it would be better to castle kingside, because then you would have all of your pieces coordinated in one attack. Queenside castling would leave the bishop and queen slightly excluded due to white's pawn structure, reducing their effectiveness in a pawn attack on the white king.