Which side to castle in caro-kann?

In the classic caro-kann I see games where black castles queenside and kingside both fairly common. what are the advantages of each of these and which should generally be better? do they each have unique plans?

I am not expert who can break down any key points or a point, at which it is imparative for you to castle to one side or the other. I would simply say that, even without calculating anything, from a strategy stand point, if you can see any sort of positional advantage, that gives you better attacking chances with a pawn storm, your minor and your major pieces, while being able to hold the fort together, going queenside could certainly be an advantage.

I would say most players who try to memorize lines from openings/defenses, of the more popular, viable lines, such as the Caro-Kann, most likely concentrate on kingside castling lines foremost, because these positions seem to be more often played. This could possibly level the playing field. While watching two of the best players in the world play each other. I noticed they both tried to throw everything, including the kitchen sink at each other.

To try to answer a few of your secondary questions. Kingside castling is generally easier to obtain quicker. This is often the reason it is chosen. Keep in mind, you do have opportunities to try to steer the game to either direction for different reasons. You could do it to try to throw your opponent off, perhaps to make em guess what you are up to. I like to leave myself options personally.

I find, with each choice that your opponent makes, they give you something you can use, or something in their position, that can be exploited somehow. Try to learn how to see this to help you make your determination. Try to take what your opponent gives you, in addition to to trying to force them to relinquish what you want to take.

If possible, make all of you moves have two fold consequences for your opponent. Don't give them one thing to defy. It forces them to use all of their resources for defense, instead of offense. Once they are defensive, their options will help you to determine how to attack for mate.

White should be better in the caro kann. But black will have a better endgame due to the pawn structure.

What makes black's pawn structure that much better in the caro?  I think that depends on the variation you play...

I dont think u answered his question. No offence btw. 

You failed to realize, I wasn't answering it to satisfy you. You opinion is irrelavent to me. I think you need to go back to the drawing board.

True. But in the classical caro kann, It is known that black will usually have a slight edge in the end game.

@Chess4001 That's a very good question. I can't verbalize an answer to it, but I can recommend a DVD that will probably help you form some informed opinions on this subject: "Knowing The Terrain Vol. 2: The Capablanca Structure" by IM Sam Collin. What I love about Sam's "Knowing The Terrain" series is that he doesn't judge any general idea as totally good or totally bad: Instead, he presents numerous examples for each major thematic idea in a chosen structure and shares his observations and ideas.

Look, you might know enough to make me look like an idiot in general, as well as, play circles around me but, it is apparent that your either don't read so well or think the OP and I both came here to have you enlighten me on the finer points of the Karo-Cann. I already stated. I am no expert. I wasn't trying to give the OP an expert breakdown of at what point in each line of the Karo-Cann, that one must castle and to which side.

I guess you also didn't take from the OP's 1st post that perhaps he/she isn't acutely aware of the best way or time in general to determine the best time and side to castle, for any opening or position. I was simply trying to give him/her the information to help reason through the process for this.

If you don't like my strategy or analysis. Don't I didn't develop it to suit you.

He responded to my post, which is true, I forgot about the classical line with h4 stuff.  The last few times I've faced it, I've faced 4...Nf6 with 5...gxf6 and it's black's pawn structure that's in question :)

U should take a chill pill. And look at his rating, im sure he knows all the basic stuff like develop pieces castle etc. 

Can I get those over the counter or do I need a prescription? Is my question an admission of needing one or my ability to have a sense of humor when you say I am all worked up. My advice to you is learn a better approach to people in an "A" to "B" conversation. It is rude to suddenly approach uninvited and start criticising someone's ideas, as if you know exactly what they are thinking. It isn't only rude, it is insulting to other peoples intelligence.  You expect me to stop, bow and applaud? I think it is you who needs to check himself...

As white, I tend to really like playing against the ML Caro when black castles kingside...  There's often a knight sacrifice on h6 that gives white all of the fun.

Here's an example variation, very similar to an OTB game I played with white:

As a Caro Kann player of many years - I think the key with regard to castling is the defence of the g7 point. 

In the Spassky variation (4...Bf5) sometimes you may want your king to guard this square - especially if the white knights are headed to the kings side.

In the Bronsted-Larsen (4...Nf6 and 5...gf6) you can play some very solid lines with 0-0, Bg7 and Bf5-g6.  But most black attacks in this variation are based on the open g-file so 0-0-0 is more common.

I have never played 4...Nd7 but suspect it is similar to the Spassky line - with castling possible on both sides - depending upon how solid you wish to play it.

The Panov-Botvinnik and Advance variations most commonly have 0-0.

hope this helps.

DD.

The Caro-Kann is an impenetrable underground bunker that is used by otb tournament players as their opening weapon when they need a draw, when their standing is 2-0, and they are up against the strongest player in the section they are playing in.  It is an invaluable weapon for holding your ground in the standings in the 3rd or 4th round. 1/2 a point goes a long way to keeping you in contention to place or share 1st in a tournament.

If White wants to bloody himself on the brick wall of the Caro-Kann, let him.  At some point he will overpress for advantage and find himself in an inferior position.  As Black you should play solid and boring moves.  Every move designed to equalize.  The onus is on White to prove that, because he has the first move, he should win.

The best advice on castling quennside or kingside was given to you by DoubleDum.     

Just like Anand doesn't give away his preparation to Gelfand and vice versa.  And, tournament players don't give away their preparation to other players in the tournament.  I won't give you part of my opening repertoire preparation just to prove that, "I would agree with you, if you were right." 

I agree with transpo.

Generally kingside, but queenside can offer some interesting attacking possibilities. However, you will need to use some time to get your king to a8.

As an experienced caro cann player the rule of the tumb should be to castle the same side that white does. Caro Cann might seem like a bunker but with oposite castling white is often faster (ofcourse there are some lovely exceptions in that such as the game tal vs pertrosian).

Ofcourse  castling the same side might run into tacticle probloms specialy round f7 if you blindly follow your oponent and catle long.

Great game last week between Kamsky and Seirawan where Seirawan played the Spassky variation, castled on opposite sides and got murdered by a viscious attack down the g-file.

DD