When do you "double step" a pawn?

I am not sure if there is a name for this, but there should be. I'll call it a "double step". This is where you initially move a pawn one square in the beginning and soon after you move it again breaking the beginner's rule of not moving the same piece twice early on in a game. If this does not apply to all pawns, then I am specifically talking about the d and e pawns at least.

In the following position, Stockfish shows e6 is the best move. Then, it shows e5 later. So, what new rules/guidelines can you use to break the beginner rule to not to play the same piece twice early on in a game?

That is a horrible example by the OP because Black's play sucks!  You do not develop the Knight early to c3 (white) or c6 (black) when dealing with QP openings.

A better example is in the Caro-Kann Defense, and the reason is self explanatory, and the key difference between the Caro-Kann and the French.

1.e4 - Black needs to contest the center so as not to allow White totsl domination.  He can play for control of d4 with 1...e5 or 1...c5, where if White plays d4, Black will take so as not to give White central domination.

The other option is to play for ...d5, but a prep move is needed so that if White takes on d5, Black can recapture with his pawn and not his Queen, bringing out the Queen to early.

However, how do you prep it?  Here inlies the difference between the French and the Caro-Kann.

French - Black plays 1...e6 to prep 2...d5.  The cost of this is that White can block the e6-pawn, which will hem in the Bishop behind his own pawn chain.  In return, once White advances e5, whether it be move 3, move 4 in the Winawer, move 4 in the Tarrasch, or move 4 in the Steinitz, Black can contest the pawn in the back (d4) with the move c7-c5 in one go.

The Caro-Kann, 1...c6, also covers the d4-square, and leaves the Bishop open to develop outside the pawn chain with ...Bf5 or ...Bg4.  The cost of this is 2-fold.  Light squares on the Queenside, particularly the e6-pawn, are weak and the also, Black has almost no counterplay without ...c5 played to hit the White center, but in return for getting the Bishop out, Black had to spend 2 moves on the c-pawn to get to c5.

This is why you sometimes see a pawn move one square twice within the first 10 moves.

"You do not develop the Knight early to c3 (white) or c6 (black) when dealing with QP openings."

Yes, I agree with that general idea. When white plays d4 I usually don't do that unless I am completely distracted, chillin, and not playing a serious game. I still often play e6 and wait to decide on c6 or c5 depending on what they play next and prepare Nbd7 for a near future move. Bad approach? So far it seems to give me good results in the opening with QGD/Slav lines. 

"However, how do you prep it?  Here inlies the difference between the French and the Caro-Kann."

I was black and had no intention of playing either French or Caro Kann as black. My resources tell me the game was a "Reti" which I was not reti for.

The game went: 1.Nf3 d5 2.e3 Nc6 3.d4 Nf6 4.c3

Ok, so 2...Nc6 is not a good start and white can play d4 as they did. But it doesn't appear to be a blunder. There is still play to be had at the lower club levels.

"That is a horrible example by the OP because Black's play sucks!"

Yes, at higher levels lower level players often suck. We could say that about many lower level games and higher level blunders or questionable moves. 

If you don't want to address lower level play, that's fine. You don't have to. You can spend time wondering why Qa1 was played by the greats.

Regardless how sucky Nc6 was, I still want to understand how "goody" e5 is.

Sheesh - I never said your game was a French or Caro-Kann.  You asked about the concept of moving a pawn a single square twice early on.

It is called giving a LEGITIMATE EXAMPLE.  The fact that you game may have been a Reti is 100% irrelevant!  You asked about a concept.  I answered the concept with a legitimate example.  You apply the idea in any opening or game where it is relevant.  You must have a reason to take 2 moves to do it.  I explained that in the Caro-Kann, there was a legitimate reason to move c6 and then soon afterwards play c5.

If you are just trying to do it for your health so that you can say you did it, you will get nowhere in chess.  That is like saying I am going to put a Knight on the rim just to be cool!  There will be legitimate cases to put a Knight on the rim, but do not force the issue.

Same here, do not just try to force the issue in specifically a Reti.  If there is a legit time to move a pawn once and then move it again, do it.  If you ever decide to play the Caro-Kann, you will do it a lot, but you will also see it in other openings.

Read post two from a concept perspective, not a specific opening perspective.

Another type of position in which the "double-step" makes sense is when you induce a weakness in the opponent's Pawn structure.

"Sheesh - I never said your game was a French or Caro-Kann. You asked about the concept of moving a pawn a single square twice early on."

Your words implied it. Don't want people to read it that way? Don't type French or Caro Kann.

"The fact that you game may have been a Reti is 100% irrelevant!"

Then that shows you have an agenda not to address the Reti game I asked about. If I went into a store and asked how to change the screen size and resolution of an android device, I wouldn't want the store to tell me how to do it on an iphone. Your advice might be relevant to how you read my question, but it is actually irrelevant when it pertains to my question even though we are answering the same question from different angles.

Like how I used your word against you? Bring it on!!!

"I answered the concept with a legitimate example."

With that logic, you should sell Aladdin DVDs to rug owners then.

"I explained that in the Caro-Kann, there was a legitimate reason to move c6 and then soon afterwards play c5."

"I never said your game was a French or Caro-Kann."

Do you always use other examples that don't pertain to the context of the question at hand? When I asked about e5, I wasn't asking about any situation. I gave the actual FEN position. If I wanted a general discussion, would I have inserted the FEN? (audience: No he wouldn't have!!)

"If you are just trying to do it for your health so that you can say you did it, you will get nowhere in chess."

I have no idea what that means. Asking about a position in a game is like doing something for my health? Please do expound.

"That is like saying I am going to put a Knight on the rim just to be cool!"

Well, the difference is that e6 is a (more) normal move. N to the a or h file early on is not a normal move. This is why I stated, "If this does not apply to all pawns, then I am specifically talking about the d and e pawns at least."

"If there is a legit time to move a pawn once and then move it again, do it."

Now you are hitting on the hot spot of the nail. Care to expound on that statement? 

(Interpreter: What he is asking is why e5 in the above position? He is not asking about the French, the Caro Kann, the Italian, the Sicilian, or the Annunaki. Can you explain the reasons without insulting this fine lad?)

"If you ever decide to play the Caro-Kann, you will do it a lot, but you will also see it in other openings."

Wow, you are bent on bringing up these openings aren't you? I wonder when the day will come that you realize I am not asking about the Caro Kann or the French. Let's wait and see.

"Read post two from a concept perspective, not a specific opening perspective."

Or, you could make a thread and title it "When to play e5 in the Caro Kann or the French". Do you want help with that?

This thread is about reading post 1 the way the OP intended it, by looking at the position and commenting on the position provided. Why does e5 in the position and subsequent positions show e5 as the top or one of the top moves.

Hey, I am not trying sell you crack. I don't want you to get hooked on anything, but give it a try. Why e5 in the position in the OP? 

Thank you for explaining why e5 is suggested by Stockfish multiple times in the position provided in the OP. 

*shrug*

Anyone who depends on an engine to understand opening play, fully deserves whatever garbage the engine wants to offer him.

double stepping the pawn allows the pawn teleportation glitch, onponsodont

In your example, moving the pawn two squares up was not possible earlier, because the e4 / e5 square was controlled by the opponent.

Now it is possible and it helps to gain more space in the center, opens the diagonal to develop the bishop on c1/c8 and stops the opponent from ever placing a knight on e4/e5 where it can be very powerful

That's great news because I am posing a question for humans to answer. It would be kinda silly if I asked Stockfish now wouldn't it?

I don't know if there is an award for answering someone's question directly without insulting them first, but you definitely earned one in my book. Excellent punter99!!! Thank you.

You're welcome. In general such double-steps are justified if you gain something useful in return. Like open diagonals and files for your pieces, reducing the opponents central control, etc.

So, now digging deeper, I am looking at master games where this idea of opening up a diagonal happens. I found two games. One game does this, the other goes against it. I'll post the games so people can look at it and then post later maybe with questions. Feel free to spread your wisdom on these two games which came from a collection of Zukertort openings when pulling up MVL games. I tried posting in order, but it reversed. The second game is the one that opens up the diagonal, and the first game goes against this idea with f5. So, I'll straight off the bat be looking for reasons why So played f5.

You can fast forward straight to 1:00:00 for the game. Seirawan thought to play 13...Be8 instead of Qe8 (1:03:30). Is this the usual idea if you are going to play f5 to retreat the bishop back to the 8th rank?

The first game is a bit different. MVL played a rather unique setup h4 and Qb1 with the idea to continue with Bd3 or Ng5 attacking the Black king very soon. So Wesley decided to play f5 to block the b1-h7 diagonal and slow down any potential kingside attack immediately.

Bd7 - Be8 - Bh5 is a way to develop the bishop but it's very slow and only common in the Stonewall System where Black starts with f5 at move 1.

The 2nd game is a good example that demonstrates how Black freed his cramped position by opening up the center so he could bring all his minor pieces on active squares. Otherwise the Bc8 and Nd7 would be doing nothing.

I am not sure how the Schliemann variation in the Ruy Lopez addresses either e6 then e5 (in the OP) or f5 (since e5 is already played and I posted the So game because he had the e pawn on e6).

What is your example supposed to illustrate? Example of what?

Wow, really?

That's your reply to me?

Ok, no problem.

I have plenty of people who appreciate what I offer for instruction other places.

It's ok. If you don't want to explain yourself, no one is going to chase you. 

Wait, do we have any Brits reading this thread? I heard they foxhunt.