Castling queenside

I used to castle queenside liberally, particularly when playing against a black kingside fianchetto to attack by advancing my kingside pawns. But as I've improved and run into better players I've landed my king into hot water and wondered how the hell it happened. I've become a little gun shy about it, though I do enjoy those games where you're attacking the king side and your opponent's attacking queenside and it's a race to see who breaks through first. Sometimes the board almost looks like a yin-yang Tao symbol.

I've become aware of the weakness of the a-pawn and having to spend a move to bring the king to the b square. But what are some of the general rules of thumb as to deciding whether to castle queen side? What steps should you take for protection?

And when is it appropriate for black to castle queenside? I can't think of any opening variations in which it's routinely done.

I've become aware of the weakness of the a-pawn and having to spend a move to bring the king to the b square. But what are some of the general rules of thumb as to deciding whether to castle queen side?
- you need to bring your king to safety fast and castling kingside is too dangerous;
- you need to bring your king to safety fast and only your queenside is yet developed, which means you can't castle kingside (yet);
- occupying the d-file with a rook is of great importance;
- your opponent has castled kingside and you have already made some advances on that wing.

What steps should you take for protection?
moving the king to b1(b8) is almost always necessary. After that your king's position is pretty much like you've castled short and should be treated accordingly.


And when is it appropriate for black to castle queenside? I can't think of any opening variations in which it's routinely done.
A good example is the caro-kann mainline - in this opening black always has a half-open d-file so it is logical to occupy the d-file with a rook.

Bringing the rook to the d file is certainly a plus.

But it's interesting that the queen side castling seems to take place so often in the Sicilian, when black has the open c file to attack you from, even to the point of sacrificing the rook for a knight.

Originally posted by schakuhr
- you need to bring your king to safety fast and castling kingside is too dangerous;....

I've heard that queenside castling in the Ruy Lopez Exchange isn't all that uncommon. In addition, I know the Albin Countergambit employs queenside castline fairly often, too.

Originally posted by wittywonka
I've heard that queenside castling in the Ruy Lopez Exchange isn't all that uncommon. In addition, I know the Albin Countergambit employs queenside castline fairly often, too.

Originally posted by gaychessplayer
Black often castles queenside in the Tchigorin Defense (1 d4 d5 2 c4 Nc6). Black also often castles queenside in the Von Hennig-Schara Gambit (1 d4 d5 2 c4 e6 3 Nc3 c5 4 cd cd).