Caro-Kann advance variation w/ 3. c5 dxc5 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 &amp; 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?
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.


"Opening Repertoire: The Caro-Kann" by IM Jovanka Houska (chapters 9-11)
"Playing 1.e4: Caro-Kann, 1...e5 &amp; Minor Lines" by GM John Shaw (chapter 2).
"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.