user109: OK, it has been said that one of the opening fundamentals is to castle early, but I have a dilemma with this and it may very well be a natural dilemma that has to be dealt with or there may be signs that one could look for. Here is the dilemma:
If I castle early, I feel my opponent has a slight advantage especially because now they know where to direct their pieces, but if I delay castling and my opponent moves their pieces to the one side of the board and I castle on the opposite, I feel I have gained some time because they have to work their way back to my castled side, however, I do know that if I do not castle early, I risk leaving my king wide open.  Further light on this would be helpful.

user2001: The purpose of castling is to protect your king. Yet, the opponent can wait with castling to see which side you will castle and then launch a pawn assault on that flank. This is possible, because the opponent can later castle on the opposite side. These types of positions are known as "positions with opposite castling" and they have a special place in terms of middlegame strategy. My advice would be for you to wait for your opponent to castle and then castle on the opposite side and launch a pawn assault on the opponent's king. Practice these types of positions and learn about them by examining grandmaster games and studying books on the topic. Another strategy is to castle queenside as quickly as possible and then control the center as well as possible with pawns and light pieces. If the opponent castles queenside too, then you just play as normal. If the opponent castles kingside, launch a pawn assault (g and h pawns) and try to open the g-file or h-file for your rooks.

user19861: If you are an inexperienced player (<1900) you should castle quickly. Yes, you may get crushed occasionally by a stronger player but you probably will lose those games anyway. 
Players above 2000 can get away with leaving their kings in the center (usually)because they understand the types of positions they can get away with it in and can see the attacks coming several moves ahead. 
I have a very aggressive style and I can guarantee I'm far more likely to win against inexperienced players if they don't castle. In fact, a large part of my rep is devoted to preventing the opponent from castling. I will sac pawns in a heartbeat and often pieces to keep the king in the center. That should tell you something. 

user46: This is from the perspective of "concrete" chess:
In modern chess, there is no hard or fast rule, it all boils down to calculation and prep. As world champion Anand has demonstrated in his match against Kramnik: this and this (just two games later, and again with Black!), it is the results that matter. So don't worry about castling early or late, but whether you are finding the strongest moves and are satisfied that you have worked out the tactics that are befitting your playing level.

user107: Here I'll provide you a good example of castling too "early". In the Pirc Defense, Black will usually get roasted in the line
[fen ""]
1. e4 d6 2. d4 g6 3. Nc3 Bg7 4. Be3 Nf6 5. Qd2 O-O?!

In this line White has not castled yet, and with the queen-bishop battery can just swap off bishops by playing Bh6, followed by f3, g4, h4-h5 to ditch the h-pawn and then play Qf6+, etc. with a tremendous attack. 
But, the point to remember in general is not to castle into an attack for no good reason or compensation.

user17: The idea is not to castle early or late. The idea is to castle when it supports the rest of your strategy.
In some games, you want to emphasize quick development, especially if your opponent has lost time. In that case, early castling is a feature of that development.
On the other hand, if it's a game with emphasis on maneuvering, you may want to delay castling until your maneuvers are complete (or nearly so), in order to use castling to support your maneuvers.

user16: I think you outline the balance well, that is what it is. You are talking about attempting to misdirect an opponent. In any game, misdirection is a dangerous tactic that takes skill to know when to make your move.
If you can get to know your opponent you can try to judge how they will move on you. If you are dead set on castling to a particular side, and your opponent knows that, then delaying doesn't help you at all.
The best solution is to remain flexible and let your opponents over or under steps dictate which tactic to use. This is as true for when to castle as anything other tactic.

user47: The answer is twofold - learn your opening theory, and learn how to defend.
If you can defend yourself against the attack, then you're not "castling into the attack", you're simply castling.  Of course, you could be wrong, and castling could be a mistake, but that's chess - you have to make trade-offs, trust your instincts, and calculate the position.
In most openings, opening theory tells us whether the risk/reward trade-off of castling on a given side of the board is worth it.  You never see white castling queenside in the Grunfeld, and that's because we know from opening theory that it's too risky.  An advanced study of the French and Sicilian defenses helps a player gain a better intuition for when it is and is not okay to castle kingside.
Sometimes, of course, we don't even know, and castling is a gamble.  In the Sicilian and Caro-Kann defenses, black often castles kingside without being sure whether or not it's a suicide move, and hopes that his counterplay and defensive abilities are stronger than his opponent's attacking abilities.
There really is no way to say "in positions with these features, you can castle, and in positions with these features, you can't" unless you're a computer playing computers.  Learn opening theory so you can get a good intuition for when it is and is not okay to castle (If you think it might be, it probably is) and then become a better defender so you can defend yourself against whatever attacks your opponents may choose to throw at you.  Unless you're playing Houdini or Kasparov, your opponent is unlikely to execute his or her attack perfectly, and it is a test of skill rather than a positional decision.
Of course, sometimes it's really obvious that you shouldn't castle, like when you have a totally fractured kingside.  But categorizing such positions would be pointless because what matters is context.  Similarly, if all your opponent's pieces are on the kingside, that's also a sign that you shouldn't castle there.  You have to have faith in your defensive abilities, though, otherwise you'll find yourself being afraid to castle just because your opponent played 1. h4.

109: <p>OK, it has been said that one of the opening fundamentals is to castle early, but I have a dilemma with this and it may very well be a natural dilemma that has to be dealt with or there may be signs that one could look for. Here is the dilemma:</p>
<p>If I castle early, I feel my opponent has a slight advantage especially because now they know where to direct their pieces, but if I delay castling and my opponent moves their pieces to the one side of the board and I castle on the opposite, I feel I have gained some time because they have to work their way back to my castled side, however, I do know that if I do not castle early, I risk leaving my king wide open.  Further light on this would be helpful.</p>
 2001: <p>The purpose of castling is to protect your king. Yet, the opponent can wait with castling to see which side you will castle and then launch a pawn assault on that flank. This is possible, because the opponent can later castle on the opposite side. These types of positions are known as "positions with opposite castling" and they have a special place in terms of middlegame strategy. My advice would be for you to wait for your opponent to castle and then castle on the opposite side and launch a pawn assault on the opponent's king. Practice these types of positions and learn about them by examining grandmaster games and studying books on the topic. Another strategy is to castle queenside as quickly as possible and then control the center as well as possible with pawns and light pieces. If the opponent castles queenside too, then you just play as normal. If the opponent castles kingside, launch a pawn assault (g and h pawns) and try to open the g-file or h-file for your rooks.</p>
 19861: <p>If you are an inexperienced player (&lt;1900) you should castle quickly. Yes, you may get crushed occasionally by a stronger player but you probably will lose those games anyway. </p>

<p>Players above 2000 can get away with leaving their kings in the center (usually)because they understand the types of positions they can get away with it in and can see the attacks coming several moves ahead. </p>

<p>I have a very aggressive style and I can guarantee I'm far more likely to win against inexperienced players if they don't castle. In fact, a large part of my rep is devoted to preventing the opponent from castling. I will sac pawns in a heartbeat and often pieces to keep the king in the center. That should tell you something. </p>
 46: <p>This is from the perspective of "concrete" chess:</p>

<p>In modern chess, there is no hard or fast rule, it all boils down to calculation and prep. As world champion Anand has demonstrated in his match against Kramnik: <a href="http://www.chessgames.com/perl/chessgame?gid=1510272" rel="noreferrer">this</a> and <a href="http://www.chessgames.com/perl/chessgame?gid=1510508" rel="noreferrer">this</a> (just two games later, and again with Black!), <em>it is the results that matter</em>. So don't worry about castling early or late, but whether you are finding the strongest moves and are satisfied that you have worked out the tactics that are befitting your playing level.</p>
 107: <p>Here I'll provide you a good example of castling too "early". In the Pirc Defense, Black will usually get roasted in the line</p>

<pre><code>[fen ""]
1. e4 d6 2. d4 g6 3. Nc3 Bg7 4. Be3 Nf6 5. Qd2 O-O?!
</code></pre>

<p>In this line White has not castled yet, and with the queen-bishop battery can just swap off bishops by playing <code>Bh6</code>, followed by <code>f3</code>, <code>g4</code>, <code>h4-h5</code> to ditch the h-pawn and then play <code>Qf6+</code>, etc. with a tremendous attack. </p>

<p>But, the point to remember in general is not to castle into an attack for no good reason or compensation.</p>
 17: <p>The idea is not to castle early or late. The idea is to castle when it supports the <em>rest of your strategy</em>.</p>

<p>In some games, you want to emphasize quick development, especially if your opponent has lost time. In that case, early castling is a feature of that development.</p>

<p>On the other hand, if it's a game with emphasis on maneuvering, you may want to delay castling until your maneuvers are complete (or nearly so), in order to use castling to support your maneuvers.</p>
 16: <p>I think you outline the balance well, that is what it is. You are talking about attempting to misdirect an opponent. In any game, misdirection is a dangerous tactic that takes skill to know when to make your move.</p>

<p>If you can get to know your opponent you can try to judge how they will move on you. If you are dead set on castling to a particular side, and your opponent knows that, then delaying doesn't help you at all.</p>

<p>The best solution is to remain flexible and let your opponents over or under steps dictate which tactic to use. This is as true for when to castle as anything other tactic.</p>
 47: <p>The answer is twofold - learn your opening theory, and learn how to defend.</p>

<p>If you can defend yourself against the attack, then you're not "castling into the attack", you're simply castling.  Of course, you could be wrong, and castling could be a mistake, but that's chess - you have to make trade-offs, trust your instincts, and calculate the position.</p>

<p>In most openings, opening theory tells us whether the risk/reward trade-off of castling on a given side of the board is worth it.  You never see white castling queenside in the Grunfeld, and that's because we know from opening theory that it's too risky.  An advanced study of the French and Sicilian defenses helps a player gain a better intuition for when it is and is not okay to castle kingside.</p>

<p>Sometimes, of course, we don't even know, and castling is a gamble.  In the Sicilian and Caro-Kann defenses, black often castles kingside without being sure whether or not it's a suicide move, and hopes that his counterplay and defensive abilities are stronger than his opponent's attacking abilities.</p>

<p>There really is no way to say "in positions with these features, you can castle, and in positions with these features, you can't" unless you're a computer playing computers.  Learn opening theory so you can get a good intuition for when it is and is not okay to castle (If you think it might be, it probably is) and then become a better defender so you can defend yourself against whatever attacks your opponents may choose to throw at you.  Unless you're playing Houdini or Kasparov, your opponent is unlikely to execute his or her attack perfectly, and it is a test of skill rather than a positional decision.</p>

<p>Of course, sometimes it's really obvious that you shouldn't castle, like when you have a totally fractured kingside.  But categorizing such positions would be pointless because what matters is context.  Similarly, if all your opponent's pieces are on the kingside, that's also a sign that you shouldn't castle there.  You have to have faith in your defensive abilities, though, otherwise you'll find yourself being afraid to castle just because your opponent played <code>1. h4</code>.</p>
