Castling

A member of my chess club posed a question, “If white castle on queen’s side, which side will be better for black to castle on?” To add on to his question, when if at all should you castle along with which side after white castles queen’s side?

This is highly subjective. I look out for attacking opportunities as well as king safety.

In general, you are probably looking for highly brutal attacks on both wings (White attacking Black's kingside while Black does the same on White's queenside) if Black opts to castle kingside and you are looking into a slower, more positional game by castling queenside.

If you feel that castling is a little too early or bad in a given turn, you can choose to postpone the castling or even not castle at all.

Again, it depends on the specifics of each game.

There is no correct answer. In some Sicilian lines, white castles queenside. I have castled queenside against that,  once, and won, but white played an innacuracy shortly later, but before I'd already castled kingside... but normally it has kings are on opposite sides of the board with that line. In any event, I had switch the attack to the kingside immediately, before white got his ducks in a row.

That particular line is monster tactics and my win rate as black is about 60 to 65 percent, against someone rated close to me.

I like tactical games.

If your afraid of an all out war with you opponent, avoid the sicilian. Even a "quiet" sicilian line is going for tactical fireworks at some point.

opposite side castle = attack (both sides can easily throw all their pawns up opposite wings without worrying about weakening king position) same side castle = solid (much harder to justify launching pawn storms when it jeapordizes king safety) this isn't always true though and some positions have specifics.. for example lots of Ruy Lopez will have same side castle with brutal attacks and pawn storms

Let’s take a look at when it makes sense to castle opposite sides and when it doesn't.

You should castle on the opposite side when at least one of the following factors is true:

1. When you are up in development and your opponent has already castled, you should consider castling in the opposite side. That way you will have a clear game plan and will also be able to capitalize on your development advantage.
2. When you have a damaged pawn structure (doubled paws, missing pawns, far advanced pawns, etc.) on one of the sides you should consider castling on the other side.
3. When opponent’s pieces are especially active on one side of the board, it is usually best to castle on the opposite side.
4. If you want to complicate the game you may consider this option. That may be true if you must play for a win due to a tournament situation, when the draw is not enough. Also that maybe done when you're playing against a stronger opponent, who is much better in simple/technical positions. That maybe your best bet.

You should not castle on the opposite sides when at least one of the following factors in true:

1. When you are behind in development and you need extra time to develop your pieces, it is usually not a good idea to give your opponent a straight forward way of launching an attack.
2. When the opponent’s pawns are advanced towards the side you’re about to castle, it is not a good idea to castle there (especially if the opponent’s king is castled on the opposite side). It will just give him a positional edge in the attack.
3. When there are open/semi-open files in-front of the side you’re about to castle, you should probably reconsider your decision to castle there (especially if your opponent has castled on the other side). That will give him more attacking possibilities, such as rook lifts, various sacrifices, doubling of pieces on the file, etc.
4. If you playing against a weaker opponent you may want to avoid castling opposite sides, in order to avoid sharp game and keep everything under control.

Note: These are general rules, not laws, meaning that there are always exceptions to them. When you’re making a decision what side to castle you should always take your time and evaluate all “pros” and “cons” and base your decision upon your own analysis. This is a very important decision. It pretty much dictates which way the game will continue. Take your time and think twice.

Other than certain lines where queenside castle is part of the line, often a person chooses a queenside castle because they didn't castle kingside in the early opening phase, in the first 5 to 7 moves, and thus either has to delay castling entirely, which is how late endgame castling becomes weaponized, or they castle queenside because a kingside castle would be detrimental to their game.

Of course, a person might choose a queenside castle just to surprise their opponent, but that's more likely to be done at a club level and not in a serious game.