When to play d5 or e5 in the Najdorf?

Does anyone have any good rules of thumb to follow about when to play d5 or e5, as black, in a Najdorf type setup? Or a good video on this topic?

I play the Najdorf but feel like I never have any idea when I should be pushing my d or e pawn.  

Can you give examples of your "Najdorf type setup"?

The e-pawn may be easier to answer than the d-pawn.

d5 is a crucial question.

Traditionally, the ideas has been that in a "true" Najdorf, one plays e7-e5 immedieately, on move 6, except against 6. Bg5 and 6. Bc4 where the move would be positionally wrong.  While 6. ... e6 is certainly possible against other moves, it's typically thought of as a transposition to a Scheveningen.  Are you thinking of those "Schevenengen-Najdorf" positions?  There, e6-e5 isn't a typical idea, and no examples are comming to mind immediately, though there probably are some.  (There's also the 6. Bg5 Nbd7 line where white holds off on moving the e-pawn at all, partly in the hope of creating conditions where e7-e5 can be made playable.)

I've just gotten Herman Grooten's recent "Sicilian Structures Part I: Najdorf and Scheveningen," which addresses these sorts of pawn-structure questions at considerable length.  Despite the length, though, it's concerned iwth general condiderations within each of the major Najdorf and Scheveningen lines rather than with building a precise variation tree.  I've only just started reading it, but what I've read so far is helpful.

Here is an example from a recent game I played. On move 7, I played Bb7, which was a mistake, and I should have played e5 according to the engine.  I should have known that, but didn't.

Here's a second example, where I again play Bb7, but d5 is slightly better according to the engine.

I wouldn't think b5 is a big mistake here.  In some lines, white has a good way to punish a too-early b5, but I don't see one here.  (Often, it involves a queen winding up on d5, which is harder after Bd3.)  Still, e5 is more common here for the normal Najdorf reasons, plus the fact that white has even less control over the potential d5 hole than in other lines.  Other moves are possible too, e.g., g6 and Nc6, in one order or the other, since White now can't get to a proper Yugoslav setup, and since the queen can't support the knight on d4.

 Interesting. Maybe I am playing e6 too much, when I should be playing e5 instead. 

It's completely a matter of taste.  Kasparov liked the e6 lines, so you're in good company.

More than likely, after White's response to your choice of Najdorf, you're going to develop the e-pawn.

Those mentioned above and if (for example) 6.Qd3, you can play either 6...e6 or 6...e5 like said it depends on the type of "structure" you prefer (not getting into refutations or what's better).

Some nowadays call some of structures "Najdorf", but earlier versions were actually called "Boleslavsky Hole" (because of d5).

Your b5 idea was natural (if plan was to move the knight from c3 before Nd5 can be played).

I'll post some typical plans in a bit.

• Placing a knight on d5, after sure always able to recapture with a piece, and not a pawn
• playing c2-c4 to protect a piece on d5
• Pawn break with f2-f4 (common with opposite side castling)
• Remove the defenders of d5 by:

1. advancing g2-g4-g5 to kick the f6 knight
2. playing Bg5 and Bxf6 to eliminate the f6 knight
3. playing f2-f4-f5 to prevent the DSB from reaching e6, or to remove it

• Attack on the kingside (pawnstorm)
• Pressure the weak d6 pawn and the d-file

• Pawn break with d6-d5 to solve the structural issues, fight for initiative, and advantage in the centre 
• Prevent the c3-knight from going to d5:
• Playing b7-b5-b4 in order to displace the c3-knight before it can go to d5
• Pressure the c-file to pin the c3-knight to the c2-pawn
• Minority attack on the Queenside
• Exploit the c4-square (sometimes with a rook)
• Obviously, defend the backward d5 square with pieces

Thanks! I appreciate the tips!

I just noticed the Alapin game...

Brings up why I asked about the "Najdorf type setup".

You can't always just play a certain "setup" against anything. You can, but it'll cause you problems.

Notice d5 is not so hard to play in that variation but is in a Najdorf