I like to play the Caro-Kann as black, and in response to the advance variation play 3... c5!? This works really well for me (~1800 USCF), but as I've gotten better I'm being forced to deal with the response which is common at higher levels, which is 4. dxc5! Nc6 leading to a position which I've found uniquely uncomfortable (and after only 4 moves!):

[FEN "r1bqkbnr/pp2pppp/2n5/2PpP3/8/8/PPP2PPP/RNBQKBNR w KQkq - 1 5"]

Although the computer thinks Black is okay (stockfish depth 29: +0.5) this opening feels very different from other variations of the Caro-Kann and as such I've felt recently that I should study the variation in more detail, but I've really struggled to become more comfortable in this position despite putting more time into this position than almost any other in my repertoire. Here are the reasons that I can see why I'm having trouble:

  • Fundamentally, black is cramped and down a pawn. Worse, in many variations persist for a long time even with perfect play. Proving compensation seems very hard.

  • There are a bazilion ways white can play which keep this cramping theme - at almost every move there are 5 moves within a half evaluation point of each other, and my opponents tend to break from the "main lines" that I can see in opening explorers very quickly. Memorizing moves & responses feels fairly futile past a couple moves, and these lines usually don't lead to what I'd call a "comfortable" position.

  • If I'm not very careful, White's queen-side majority can create passed pawns and with such a cramped position, this can prove deadly. I've lost several games in this fashion.

  • I've struggled to find much theory or discussion of this position since 3... c5 is it's a 10-to-1 side-line of the main Caro-Kann (although I'm probably just not looking in the right places). The couple books I've looked at don't cover 3... c5.

So, I'm looking for some advice from more experienced players. How can I study / improve this opening? Am I thinking about something wrong here? Is this just a fundamentally uncomfortable position (and probably the reason 3... c5 isn't the main line) and I should just accept that and play a different opening if it's too much? Should I just bunker down and spend a lot of time memorizing lines to guide myself through the opening stages here? I've struggled to gain much insight by looking at pro games (and this is played occasionally at the highest level), but maybe I should try harder at a that?

  • 1
    For decades, the Caro was my main e4 defense. I will answer, but I have a few questions to ask first. First, is there a reason you don't play the mainline 3...Bf5? If you are getting un-Caro-like positions that you do not like, this is one way to get more Caro-like positions. Second, what type of player are you: Positional, tactical, or universal (play both styles often)? Lastly, and this is important: How old are you? This is important because, if you are under 25-ish, leading you down a tactical variation is fine, but if you are my age, 58, then you want to avoid such positions. Commented Nov 23, 2019 at 22:35
  • Hi @PhishMaster, 1. To be honest, my original motivation for trying the sideline was that Ben Finegold recommended it at some point, and that I have had a lot of personal success and fun positions playing against 4. c3 or 4. Nf3. 2. I think I'm much better at positional chess, I feel like I blunder tactics way under my rating. But I'm trying to get better at that, which discourages me from going for the main line which I think of as less tactical. 3. I'm 26, but I just started getting into chess a couple years ago, so I still feel like a newbie :3 Commented Nov 23, 2019 at 23:07
  • 3
    This isn't an answer to your question, but I'm wondering why you play 3...c5 in the first place. You seem to dislike being down a pawn and also don't want to deal with the many ways your opponent could choose to play in concrete situations. These are factors inherent to the 3...c5 line, especially considering that 4.dxc5 is the main move (both in my reference database and correspondence db). Is there a reason you dislike 3...Bf5? If solidity is your aim that move seems better suited to your purposes. Commented Nov 24, 2019 at 10:47

2 Answers 2


OK, after reading your reply to my question above, I can more accurately answer.

First, contrary to Fuxia's comment, the move you played, 4...Nc6, is actually more popular now at higher levels than Botvinnik's 4...e6. To quote GM John Shaw's 2016 book:

4...Nc6 is more popular these days and can be viewed as slightly more ambitious, as well as somewhat riskier. It can lead to exceptionally sharp play....

Thus, based on your answer above, I would not play 4...Nc6 since it simply does not suit your style. If you are going to play 3...c5, then I would play 4...e6 as it leads to more positional lines, that are easier to understand. Also, not that you are old, but if you are having problems with blundering, going into sharp lines with 4...Nc6 may be suicide.

Here is what I would recommend:

  [FEN ""]

  1. e4 c6 2. d4 d5 3. e5 c5 4. dxc5 e6 5. Nf3 (5. Be3 Nh6! {This is actually very positional since if white takes, most of the lines favor the black bishops.}) (5. a3!? {Shaw}) Bxc5 6. Bd3 Nc6 7. O-O Nge7 {with the idea Ng6, Qc7, and maybe f6 after O-O. Also, instead of Qc7, you can also play Bb6-c7 with the same type of pressure on e5.}

Now, in any case, that is barely touching the surface. If you want to play that line, you will need to look at more specific material. Here are some study materials.

  1. "Opening Repertoire: The Caro-Kann" by IM Jovanka Houska (chapters 9-11)
  2. "Playing 1.e4: Caro-Kann, 1...e5 & Minor Lines" by GM John Shaw (chapter 2).
  3. "Practical Black Repertoire with d5, c6. Volume 2 The Caro-Kann and Other Defences" by GM Alexei Kornev (chapter 6+7)

All three books have advantages, and all are pretty new, having been published in 2015, 2016, and 2017 respectively.


This line, the Botvinnik-Carls Defense, is my pet opening as Black. :)

The critical move after 4.dxc5 is e6! If White tries to hold the pawn with Be3, you answer that with Nd7. In many lines after that you have a way to get the pawn back or get the bishop pair and a much better pawn structure.

See the annotated example below.

[Result "*"]
[Annotator "https://lichess.org/@/fuxia"]
[UTCDate "2019.11.23"]
[UTCTime "21:48:33"]
[Variant "Standard"]
[ECO "B12"]
[Opening "Caro-Kann Defense: Advance Variation, Botvinnik-Carls Defense"]
[FEN ""]

1. e4 c6 2. d4 d5 3. e5 c5 { The very early c5 is the beginning of the Botvinnik-Carls Defense. Instead of Bf5, Black tries to undermine White's center pawns immediately. White now has to make an important decision: to take or not to take. Looks like a gambit, but Black will very likely get this pawn back. } 4. dxc5 e6 { And not Nc6! } 5. Nf3 { Give the c-pawn back immediately, protect the center pawn on e5 instead. } (5. Be3 { One way to cling to that pawn. The same as in the 4…Nc6 line above. } 5... Nd7 { My recommendation. Attack c4 again. } { [%cal Gf8c5,Gd7c5] } (5... Nh6 { One of the main lines, but I really don't like the situation after Bxh6. GM Chirila played that once against me, and I had to face a very strong kingside attack. } { [%cal Gh6f5,Gf5e3] })  (5... Ne7 { Again, the same motif: Try to attack White's bishop on e3 with the knight. This is slow tough. } { [%csl Gf5][%cal Ge7f5,Gf5e3] } 6. c3 { Now White can dream about an exchange of that bishop on d4. This would restore its center pawns. } { [%cal Re3d4] } 6... Nd7 { Well, the other pawn is tasty too. } { [%cal Gd7e5] } 7. Nf3 { Black is really missing the light-square bishop here. This is the reason why the 4…Nc6 is so attractive for Black. } { [%cal Rf3e5] } 7... Nf5 { A nice move that creates attacks all over the place. } { [%cal Gf5e3,Gf8c5,Gd7c5] }) 6. Bb5 { prevents that for now. a6 doesn't help, because after Ba4 Black cannot play b5. } 6... Ne7 { Develop instead. } { [%csl Gf5][%cal Ge7f5,Gf5e3] } 7. c3 (7. Nf3 Nf5 8. b4 Nxe3 9. fxe3 a5 10. c3 Be7 11. O-O O-O 12. a3 Qc7 13. Bxd7 Bxd7 14. Qd4) 7... a6 8. Bxd7+ Bxd7 9. Nf3 Nf5 { [%cal Gf5e3,Gf8c5] } 10. Qd2 (10. Bd4 Nxd4 11. cxd4 b6! { Now it is a gambit. } 12. cxb6 Qxb6 { [%cal Gb6b2] } 13. Qb3) 10... Nxe3 11. Qxe3)  (5. a3 Bxc5 { Recapture, and have a nice game. }) 5... Bxc5 6. Bd3 Ne7 7. Qe2 { The best move according to Stockfish 8, depth 40. Rarely played. But e5 will be under fire soon. } { [%cal Re2e5,Rf3e5,Re2b5] } (7. O-O Nbc6 8. a3 (8. Bf4 Ng6 9. Bg3 O-O)) 7... Nbc6 { [%cal Gc6e5,Ge7g6,Bg6e5,Gd8c7,Bc7e5] } 8. O-O Bd7 { Prepare for pins from b5. This might be a novelty already. Then engine likes it more than Ng6 or 0-0. } *

In general, I think this line is Black's best response to 3.e5. And if you play it correctly, you get a very solid position and chances to develop a strong center.

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